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Captain Awkward’s Dating Guide for Geeks

Hello everyone! I’ve tweaked the format for short answer question submission (explainer for how it works is here) for these posts to keep the number & scope of responses manageable and to better guard privacy. Here’s this week’s batch of answers. Thanks to all who submitted and helped me try out the new system, I learned a lot.

Q1 Any advice on how to compliment a longtime friend in his late 20s on his intentional emotional growth without sounding condescending? I can tell he’s worked hard in the last year to become more confident, vulnerable, and considerate! So far I’ve said, “I can tell you’re in a really good place,” but I want to honor the work I can tell he’s done, you know? Thanks! (Pronouns: she/her/hers)

A1: I think “I can tell you’re in a really good place” is a wonderful way of putting it, why not leave it there for now? “I’m so glad you’re my friend” or “I’m so proud to be your friend” or “You’re so good at ____” are always in season.

If you want to say something more, try asking a question: “You seem like you’re in such a good place these days. How are you feeling/How are you doing/What are you excited about right now?” If he wants to tell you about some of the changes he’s been making, you can make more specific affirming noises then.

Sorting out our own emotional well-being is its own reward. Your friend is happier. You are happier in his company. Honor his work best by enjoying its fruits!

Q2: Hey Capt.! I recently had to move home with my parents due to financial reasons. And I know that I’m lucky to be able to! But as a late-twenty-something its a bit demoralizing. Not to mention my mother still treats me like a kid. Any tips on keeping my spirits up? Negotiating boundaries (no I will not go to church)? Not feeling like a loser for living at home at nearly 30? Thanks! (Pronouns: she/her/hers)

A2: Hi there! This is probably a good time to remind folks that US culture is really big on the idea that moving away from home and establishing one’s own household is the sole path to becoming a ‘real adult.’ On an individual basis that might be a necessary path for some of us to breathe and thrive (it certainly was for me) but it’s far from universal. Cultural traditions, disability, care-taking, and financial realities keep lots of “real” adults close to home, not to mention that there are people who like living with their parents.

It’s okay if you prefer living away from home, it’s okay to feel upset at having to move back there, it’s okay to want to go back to having your own household again, but freeing yourself from the “I”m such a loser” framework frees others from harmful, often ableist messages, too. If you can’t do it for yourself right now, could you try for the sake of other people? The good news is that you’re already practicing reframing this – “I recently had to move home with my parents due to financial reasons. And I know that I’m lucky to be able to!” – so keep doing that as you tell the story to yourself and others. “I had some financial setbacks, thankfully my parents are able to put me up.” 

There is advice on some more practical concerns in another past post:

“Be nice to your parents.  As weird as it is for you to be home, it’s also weird and awkward for them to have an adult child back in the nest.  Be extra considerate about chores.  Volunteer for things before you are asked.  Cook dinner.  Wash up.  When they give you “helpful” (annoying) advice, say “Thanks, mom, I’ll think about it.”  Even if it’s wrong, you’ll think about it, right?  Don’t pick fights, sulk, or punish them for your circumstances. Thank them for being a port in a storm for you. Take a lot of long walks away from home to give them space and privacy from you.  Make effort to seek out their company and do stuff with them – board games, cards, renting movies, taking a walk after dinner.  Ask them about their days. Treat them like adult humans who you like and not necessary evils.”

It’s harder to treat someone like a kid when they are actively participating in the household like an adult. See if you can mentally convert some of the things that were rules in childhood (like a curfew) into consideration for others (“I won’t be home for dinner tonight and I’ll text if I’ll be later than 11:00 pm.”)

As for church, and other boundaries you want to set, consider how much of setting a boundary is about having confidence in your own integrity and your own needs. You don’t want to go to church, your mom wants you to go, as long as saying “no” won’t jeopardize your immediate housing security (sadly not something everyone can count on), she can ask as many times as she likes and you can say “Mom, thanks for asking, but I don’t want to go to church. I can have lunch ready when you get home, though!” “Mom, I know church is really important to you, and I respect that, but I also know that it’s not for me, so, no thanks! Enjoy the service!” every time. If she yells at you or gets really upset? That’s her choice. You still don’t have to go, and you might be able to go a long way by modeling the behavior you expect in return. 

People often think the next step is to convince her to stop asking, but you can’t control that, and you can’t fix her feelings. What you can do is to be consistent with what you said you’d do (not go to church) and experiment treating this like a recurring caring and friendly invitation that you’re politely declining vs. a primal fight for autonomy (which on some level? It is) and seeing if your mom adjusts with some time. Mine did, I hope yours does too.

Q3. I’m so exhausted all the time, and it feels impossible to get all of my responsibilities done. Whenever I have a free moment, and try to change gears to something relaxing or fun, my partner always seems to be nearby, asking me to grab things for them or take them to a myriad of stores… and by the time I’m done, it’s time for bed. I feel trapped in an endless, exhausting cycle. Pronouns: they/them or he/his. 

A3. Hi there! I must congratulate you. So few words, so many overlapping and interconnected issues, namely:

  1. You’re exhausted all the time,
  2. You have too many responsibilities for the energy & time you have and you’re overwhelmed,
  3. When you do have some down time, your partner jumps in to schedule things and ask for help,
  4. When this happens, you don’t say no.

My suggestions for starting points or processes for addressing the exhaustion/overload piece of this are:

  1. Consider a medical checkup, esp. if exhaustion is new or has grown significantly recently.
  2. Consider tracking where your time goes for the next a week or so, without judgment or attempts to optimize things. DON’T BE FANCY. No shiny new productivity tools or or tips or hacks or apps (how would we even know which one to recommend or apply without knowing what the issue is). I’ve had good luck with a simple grid with days of the week and times of day (downloadable template) and a pencil or pen. Another even simpler way is to end your day by making a list of all the things you did. Nobody’s gotta look at this but you.
  3. Block out 2-3 hours about 2 weeks from now (after data collection) where you can be totally alone and quiet and unreachable. Libraries are good for this. Bring your filled-out grids, some blank ones, some ways to make notes.
  4. What does the data tell you? (Past insights when I’ve tried this:  Commuting and eating take up actual time/I should stop pretending I’m ever going to get up at 6:00 am/My lowest-paid/lowest reward freelance client was taking up way too much time, time to either raise rates or quit)
  5. Consider at 5 -10 possible ways you might be able to address the overall “too much on the plate” situation. Discard anything that smacks of “work smarter, not harder” or beating yourself up for not being able to do everything on your list. Keep wishes & daydreams.
  6. Sort your list. What’s one step you could reasonably take in the next 24 hours? Is anything looking juicy and quittable? What’s the worst thing that could happen if certain tasks remained undone, or got deleted from your workload?
  7. Use a fresh time grid as a planning template for the week ahead, block out obligations and things you want to do. Can you start to see ways some of this could work better? Or maybe everything is still bullshit but you can see the shape of the bullshit a little more clearly? Great! That’s enough for right now. Treat yourself.
  8. See if you can keep this going and check in every two weeks: A free hour, thinking about what you need & want to do in the week ahead, brainstorming actions & next steps, treating yourself. Repeat. My hope is that you’ll slowly regain a sense of control.
  9. Important: Probably nobody is ever going to give you time to think or plan, certainly not most employers, so you’re going to have to wrest it for yourself and guard it carefully against interruptions. People are going to be very quick to offer hacks/tips/tricks (The Pomodoro Method! Habitica! Bullet journaling! Morning pages!) and those can be useful tools but they are not a substitute for an overall process for setting boundaries around your time and giving yourself permission – this 1 hour every week, this 15 minutes at the beginning and end of every workday – to think about your life and how you want and need to live it.
  10. You may want to share your process with your partner, especially as you go, or invite them to try it out, too, but consider focusing on yourself at first, with your own schedule & priorities uppermost.

Now, here are some questions I suggest asking yourself/your partner/the situation:

  • Is your partner able to do these errands alone? If not, what alternatives exist (find a delivery service, ask someone else they know)?
  • What happens if you say “No, I’d rather not do that today, can it wait?” or “I need to close my eyes for half an hour, can I come help you then?” or “Mind handling the shopping on your own today?” Not to argue (“You always jump on me the second I get home!”), but, neutrally, as if this is a perfectly reasonable thing to ask (because it is). If you have a habit of always agreeing to help when your partner asks, is it silly that they’d develop an expectation that asking isn’t a big deal?
  • Because you are so busy in other parts of your life, do you think your partner is trying to cross the streams of spending time with you AND getting all the errands done? What are your partner’s “busy” levels compared to yours? (I can easily imagine a situation where one person coming home from work is ready to wind down for the day and someone who has been home all day is like, “You’re here! Let’s get this party started!” aka “Life with kittens.”)
  • Can you both agree to interrupt that pattern, by setting aside clear blocks of time for errands/household stuff and relaxing/date stuff?

Best of luck in finding a way to be more intentional about how you spend your days and your dates.

Q4: Some neighbours (idk who) have a cat, Bob. He liked to hang in our backyard (stressing our indoor cats to the point of peeing on a bed) until we enclosed it ($$$) Now he sits on the mesh and fights my 14yo cat through it. This week I got close enough to Bob to read their tag + phone number. I didn’t text them at 2am (last fight) What do I say, and when? Pronouns: she/hers

A4: Maybe the next time “Bob” drops by for a fight, you can snap a photo with your phone, or shoot video if you can. Then you could text the number and say “Hello, neighbor, this is [Name] at [Address.] Is this your cat, Bob? He really likes to drop by and bother my cats at night. Any way you can keep him in at night?” 

Recommendations:

  • The first time, wait until the next morning/a decent hour before you text.
  • Keep in mind that this person didn’t know about your expensive problems with Bob before this moment, they don’t have the same buildup of upset feelings. Start friendly, and focus on what is happening NOW and what you would like to happen NOW/IN THE FUTURE.
  • Keep expectations low. You’re probably not getting reimbursed for anything expensive you did to your yard. What you might get is “Can you keep Bob inside at night?” or “Hey, if Bob is being loud/disruptive, howabout I text you and you can come collect him?”
  • This vet I turned up in my Google search had some interesting suggestions.
  • I know nothing about where you live or what laws & rules about animals are like there. You should research the rules where you live and talk to people in your neighborhood. That way, if a direct request to Bob’s person doesn’t work, you can maybe find good next steps.

Moderation Note for this one: I rarely post anything about animals and animal welfare – Nicole Cliffe correctly calls this “the third rail of advice column work”- and this is why: People get very concerned about animals (a fine quality!), and sometimes also get very unrealistic ideas about what it is possible to do in regard to someone else’s animal in a way that crosses over into vigilantism or the fallacy  that the questioner is OBLIGATED to trap/steal/save Bob from his owners (an upsetting quality!). Unfortunately, “Bob” might just be an annoying quirk of this questioner’s neighborhood, and they may not have much recourse. If you’ve successfully convinced a neighbor to be more proactive about a cat situation, tell us about that! Catnapping fantasies or unfounded legal advice: No.

Q5: Whether I’m teaching my college class or explaining board game rules, people often forget small things I’ve already explained. Nbd, shit gets complicated, I clarify the thing if they ask. However, my anxiety spikes when they respond, “BUT YOU NEVER SAID THAT!! HOW WAS I SUPPOSED TO KNOW??” Correcting them seems like punching down, so I just smile and apologize and stress. Do you have any better ways to deal if/when this happens to you? Pronouns: she/her/hers

A5: If you’re pretty sure that you are covering whatever it is adequately, it might help if you think of a strange “BUT YOU NEVER SAID THAT!” reaction (vs. a simple request to repeat or review the information) as someone else’s anxiety (or other feelings-reaction) flaring up at you. Their feelings are real, but that doesn’t mean you caused them, or that their feelings are the primary thing you need to address. What’s happening is more about them than it is about you.

It still feels weird/upsetting in the moment? But maybe knowing/reminding yourself of that can help you get some distance?

In response, you don’t have to correct them, but you certainly can. And you can stop apologizing, which I think is one thing that is stressing you out. Try being very neutral and factual, like, “I did cover that at the beginning, but it’s okay to go over it again. What’s tripping you up?” 

Another thought, teacher-to-teacher: When I get the same student questions a lot, or the same part of the instructions is breaking down for people, it’s usually a sign to either create & make available or edit a written version students can refer to.

Q6: My ex is fine but definitely Ex-For-A-Reason. Occasionally they’ll reconnect and it’s great! Eventually For-A-Reason shows up and I’ll cut contact. This happened recently and I handled it well, but I’m sad to gain/lose that connection again (for good, I’m done playing emotional yo-yo). Logicbrain knows I miss idealized ex, I’m not close to many people, and I’m generally lonely (but working on it!). I did good/regret nothing, but what do I do with feeeeeeeeelings? Pronouns: she/her/hers

A6: There’s no shortcut with feelings, sorry, friend. You feel them for a while, you be nice to yourself, you give it a lot of time and space, you redirect your attention to parts of your life that are satisfying. More detailed instructions here.

Q7: I have a friend that I wish was a small-doses friend, who I instead spend an evening a week with; we take a class together and take the same train home after. I’m getting frustrated with her for invading my space, through no fault of her own. How do I manage my feelings and maintain a friendship with her when I find her annoying sometimes and see her 1000% more than I wish I did? Pronouns: she/her/hers

A7: How long does the class go? I ask because time will take care of this problem pretty soon, right? And when the class is over you can take a break. In the meantime:

  • Who do you like in the class, who makes you look forward to it? Time to quietly branch out, make sure you meet and work with some other people during class time?
  • Make a list of reasons you like this person and a list of things you enjoy talking to her about. On some train rides, ask her about those safe, enjoyable topics. Choose to engage.
  • On other train rides, could you try saying “Hey [friend], it’s been a super long day, I need to put headphones on and tune out on the way home, can we chat next week?” thank her for understanding, and grab some quiet time. Sometimes people need quiet, it’s okay to ask!

Q8: I know you’re married to a great dude after having a not-so-great history with some dudes in the past. Do you have any advice on how to feel okay and safe dating when it seems like every small thing is a red flag and every expression of intimacy is terrifying? I don’t want to override my body’s fear signals but I also don’t want to be alone forever. Already in therapy. Pronouns: she/her/hers

A8: Hi! During the winter in 2012 when Mr. Awkward luckily crossed my path, I was trying to rid myself of certain habits like sleeping with people right away, being afraid to disappoint people, or letting my essential homebody nature and inertia steer the ship too soon.

Chicago winters are harsh, liking a variety of cosy indoor activities isn’t wrong, and yet, I wanted to stop living this Marilyn Hacker poem. I wanted to stop recreating cycles of “Hi, you seem nice and like you can carry on a conversation!” followed by “Let’s imprint on each other sexually!” followed by “Eh, just come over, I made soup!” followed by either “Hey bro, don’t you have your own apartment to go to?” or “Welp, I guess you’re my boyfriend now, I can work with this.” Maybe it was time to change something up.

What I had going for me then:

  • I wasn’t new at online dating – the novelty had definitely worn off, and I had learned from some earlier mistakes.
  • We teach what we need to learn – advising others  here had helped me re-examine my own history in a gentle light and helped me articulate what I wanted.
  • I liked my life, I liked my apartment, I liked my friends, I liked my work, I liked myself, I liked being alone. This empowered me to be very, very picky.

Again, thanks to the writing I did for this site, I did put some pretty specific guardrails in place. Seven years later I can’t say for sure how much was instinct and how much was deliberate, but this is what I tried at the time:

  • Small Doses. I scheduled first dates with new people on weeknights.Why this worked for me:
    • Dates like “Want to grab some tacos after work Tuesday?” kept things centrally located, low-key, and inexpensive. If I’m already out of the house for work, no need to fight inertia or put on a special shirt!
    • “School nights” gave me ironclad reason to wrap things up early, limit or skip drinking altogether, and avoid the whole idea of going home with somebody or inviting them home with me.
    • It kept weekends free for hanging out with friends (who I already knew I liked) or enjoying time alone. If I liked someone enough to want to book up a Saturday, that was good information.
  • Slowing Down. I scheduled first dates few and far between, and after each first date, I tried to give myself some time to decide about whether I wanted another one. For example:
    • At the end of a date, I tried to say stuff like “It was really nice meeting you, thank you for coming out” instead of “Sure, let’s do this again sometime!” so I could sleep on it.
    • Before making another date, I thought about what I wrote in all the dating answers on here: Is this person as cool as my friends? Am I excited to see them again and get to know them better? Was the actual time we spent on the date fun, comfortable, relaxing? Am I at least contemplating [kissing stuff]? Were there any red flags (more on this below)?
    • Unless the prospect of a second date made me want to say a wholehearted “Yay!!!!!!!!” it was a No thank you.” And I straight up cancelled/reversed on some things if I caught myself trying to talk myself into the idea of someone.
    • If I did like someone and want to have a second or third date, I waited a long time before inviting them to my home or doing any home/cooking/cosy OR sexy stuff. Not because that’s bad (cosy evenings at my place are awesome!) but because I personally didn’t want to lapse into that mode of least resistance right away.
  • Safety and Congruence
    • Basic Safety Stuff: I met people in public places that were easy to get myself to and from. I told friends where I was going. I asked people for real names. I did at least a cursory Google search, and left that info with friends, too. I made a Google Voice number to keep my cell number private. I texted my check-in person when I arrived on the date and when I got home.
    • Intermediate Safety Stuff: I gave myself permission to bail pretty immediately if something didn’t feel right, especially if I sensed someone was a jerk or being untruthful.
      • One time a man looked at least 15 years older than his profile photo. Another man had a very different body type than he did in photos. It wasn’t that they were unattractive in person, or that I expected movie stars, but I did expect…congruence? Honesty? Self-awareness? Whatever was going on, it wasn’t my issue to dig into, so I excused myself pretty quickly and sent some extremely awkward “Look, I can’t help but noticing you look really different from your photos. Since you look fine just as you are, I hope you’ll post some recent photos before you try this again! But the discrepancy is so jarring to me, I’m just not comfortable” messages through the app when I got home.
      • Someone whose profile said “divorced” whose story morphed into “I finally told my wife I wanted to separate last week and we are still going to be roommates for a while, is that a problem?” on the actual date? = MARRIED, WHAT YOU ARE IS MARRIED, SIR. I wish that person well, I don’t think they were evil (esp. since they ‘fessed up right away when we met), I know this shit gets complicated and expensive sometimes, but I had made it clear in my profile that I didn’t want to mess with married people or anyone with an ongoing committed romantic/emotional/legal entanglement, and someone who thought they could override that or worm their way around it was not for me. Let me have informed consent, or leave me alone.
    • Sorting “Red Flags”: Dealbreakers vs. Incompatibilities vs. Questions. These are/were some of mine, provided as examples. Yours/other people’s will be different
      • Dealbreakers (Red Flags): Untruthful. Mean to the waitstaff. Brings feature screenplay to our date expecting me to give notes on it. Mansplains my job to me. Takes “no thanks” as an invitation to negotiate: (“Come on, have another drink”). Keeps trying to push the level of intimacy higher than is comfortable, talks explicitly about sex a lot or keeps bring the conversation back there even when I don’t participate or change the subject. Talks during movies. Hipster racism (which is still racism!) or casual misogyny (totes misogyny!). Negs/Backhanded compliments. Handsy, grabby, a space invader.
      • Incompatibilities (Orange Flags): Mistakes first date for therapy session, downloads a ton of sensitive/personal info on me, overshares. Conversation has no flow, I either feel like I’m performing, I’m expected to be the audience, or it’s an interrogation. Explains jokes to me. Is weird about “who pays” – either insists on paying for everything despite me holding out money, or pulls out a calculator. Every story is a rant or complaint. Making plans is difficult, requires way too many texts, person has no suggestions of activities or places to meet, lots of “I don’t know, whatever you want to do is fine!” Crosses the enthusiasm/evangelism line, i.e. If we’re on a date and you like something a lot, it’s probably fun to listen to you talk about it, even if it’s not my thing! But if you start insisting that I must like a thing, too, or telling me how much a thing I like sucks, I will endeavor to never touch any part of your body with any part of my body. Also here? “I’m not attracted to them/just not feeling it, not sure why” and “Our investment/enthusiasm levels are mismatched somehow.” 
      • Questions (Yellow Flags): Only people from their lives they mention are exes/sex partners, no mention of friends or family. Evasive answers to questions like “where did you grow up.” Any serious topic of conversation gets deflected with jokes (which, it takes one to know one, but what are we evading/avoiding?) Gaps in their story, long silences that aren’t comfortable silences.

Dealbreakers/Red Flags meant something about this person was pinging my radar where it comes to safety and/or integrity.  I didn’t want to go out with them again, and I probably would prefer not to see again in this life. As soon as I sent the “hey thanks for coming out, I don’t think we’re a good fit but I hope you meet someone great” message, I tended to block them on the dating app. And, since I had some good friends who were using the site at the same time as me,  I also sent out a few “Hey, watch out for this username, he’s pushy as hell” warnings.

People who seemed to be kind & doing their best but were just incompatible with me got filed as “Nice enough, but not for me!” Someone didn’t have to be a bad person to be a mismatch for me & what I wanted. Realizing this, and putting into practice by saying “No thank you!” to spending more time with people – even when they were very, very nice people, even when I did not want to hurt anyone’s feelings – was an incredibly powerful and healthy realization for me.

If what I had after a date were questions AND I really enthusiastically liked the person, I might give things a little more time. I didn’t need people to be cheerful or have perfect lives, and I was definitely okay with someone being reticent about painful or uncomfortable topics or a little shy (especially when meeting a stranger for the first time)(especially in contrast to people who wanted to dump all their baggage on me). If we had a second date and something still didn’t feel right? I’d know what to do.

I don’t know where to stick this in the bulleted list, but it’s another important lesson of that time: I didn’t try to convert incompatible date-people into friends. New friendships were and are for people who goddamn delight me, where I feel strong connections and enthusiasm, not an awkward dumping ground or collection plate for people I didn’t want to have sex with because I couldn’t bear to say “You’re nice, but no.” 

That’s a lot of text, right? I swear at the time, in practice, it wasn’t that complicated. All these rules/practices were about knowing myself, giving myself permission to want what I really wanted and set boundaries with myself about that.

What happened was:

I went on a bunch of first dates over the course of 6 months or so. Those ranged from “Oof, awkward” to “Eh, fine” to “Whoa, that person is a catch! He’s wonderful! But not my catch!”

I went on no second dates.

Then I went on one great first date.

And a great second date.

And all my guardrails/checks-and-balances were important because they were a reminder to myself to slow down and pay attention.

And they were a reminder to let myself enjoy things, to appreciate how good things could be. Because I felt safe, seen, respected, loved, appreciated. Because things were easy. Because I could be vulnerable. Because things matched.

So I married that one.*

I hope that helps.

Let’s do this again sometime!

 

 

*I realize this makes it sound like we got hitched on the third date. No. We got married about 4 years after we met, though I knew that it was likely/probable within a few months of meeting.

P.S. I wrote some stuff about compatibility around living space/household stuff that fits in with the whole red flags/dating someone new/is this for me? discussion here (#7).

Hello everyone!

We’re doing the thing today, where people can submit short questions at Patreon or on Twitter (@CAwkward, #awkwardfriday) before noon Chicago time and I will answer as many as I can this afternoon between noon and 2pm. Comments get turned on once everything is posted

Please enjoy this artsy photo of Daniel Striped Tiger hanging out in his new rainbow tunnel/bifrost.

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Image: Daniel Tiger inside a rainbow tunnel, walking toward camera like he’s in a Kubrick movie.

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It’s time for that thing we do, where we use the search strings people typed in to find this place as if they were questions.

First, as is traditional, a song:

Lyrics here.

1 “How to encourage husband to make friends.”

The subtext runs deep with this one, does it not? Like, where is problem originating? Is husband lonely and wanting to branch out socially and doesn’t quite know how? Is the husband treating the querent like his entire social world/cruise director/people-ing facilitator? (It happens). Is the husband fine being not very social but the querent is feeling squashed or mismatched here? (It also happens.) Did he ask for help?

I guess I would say that finding Our People is a lifelong project but Our People should not themselves be our projects. If the husband wants to make some more friends, he presumably has all the same resources that other people use to meet each other (MeetUp, hobbies, pubs, churches, sports, community theater/music, trivia night, political activism, volunteering) and all the modes of communication & social media people use to get in touch with friends from other phases of life at his disposal.

If a spouse wants to be supportive of this friendmaking effort, doing what you can to make sure there is time & money & space available for what he does want to do (“Sure, we can have a couple people over for dinner this weekend!” “Sure, go have fun! I’m gonna do my own thing tonight!” “Sure, I’ll be the designated driver, text me 20 minutes out and I’ll pick you up. Can you do the same for me on Thursday?” “Go ahead and take that art class on Saturday mornings, we’ll find the money.” etc.) is a pretty good place to start. Otherwise, he’s gotta take the lead and do the work, he’s not a toddler that you arrange play dates for or a dog you drop off at doggy day care. Also, in this process, make sure you don’t neglect your own friendships & social connections. These don’t all have to be shared.

2 “He just moved closer and now I want to break up.”

It happens. It sucks. I’m telling a story about it in Chicago this Friday.

With proximity, you have information that you didn’t have before. Be compassionate, be honest, be free.

3 “Breaking up because geography.”

Sometimes that’s a really good reason.

4 “Is it selfish to break up with my boyfriend bc I want to experience other people?”

Breaking up before the “experiencing other people” part might be the best order of operations if that’s what you want to do. I’m sure that’s not an easy decision, but what if you could make decisions about what you want without calling yourself names in the process?

5 “captain awkward how to dump someone”

Quick review:

  • You can have a face-to-face conversation, you can use a phone call or a text or a letter if that’s what you need to do to be safe.
  • Communicating your decision is more important than explaining your reasons. You don’t have to build an airtight legal argument that they agree with to leave someone.
  • Own the decision. “I’ve decided to break up.” “My feelings have changed.” “This is the right decision for me.” 
  • If they ask for reasons, that’s ok – that doesn’t make them bad people! – but you’re not a management consultant pointing out flaws in their operation, maybe you don’t have to list the complete list of their liabilities for them in a vulnerable and hurtful moment. It’s okay to say “You didn’t do anything wrong, but my feelings changed and I know I would be happier alone.” 
  • Don’t pressure the other person to stay friends with you and don’t feel like if you say “ok yes let’s be friends” that you’ve made an ironclad agreement that can never be revisited. Friendship is its own unique thing, not a holding pen for all the people we don’t want to kiss.
  • Have an aftercare plan for yourself – something where you get alone time, or see friends or family, and have space to feel sad or relieved or whatever it is you feel.
  • If they need comforting about the breakup, you don’t have to be the one who fills that role.

6 “Hi dad mom died sex”

Whatever word association game is being played here, I want out.

7 “Mum got angry at me but idk why and she wont tell me or even talk to me.”

Check out #5, here, re: The Silent Treatment.

There’s no fair way to play this game your mom is playing, so, DON’T TRY. If she won’t tell you why she’s mad, give her a wide berth. Let her silence be a gift to you instead of the abusive burden she intends. She has choices about how to communicate with you. She is making a bad one.

8 “How to tell friends you can’t afford to go out for expensive dinners.”

“I’m on a tight budget right now and I can’t afford to eat out so much, but I’d love to spend time with you. Can we do [something cheap or free] instead?” More here and here.

9 “My grandparents hate my tattoos.”

Your grandparents are entitled to their opinions but not to be jerks about it.

You are entitled to do what you will with your own body.

Sometimes a cheerful “well, good thing it’s not your body!” response works to cut down on the comments, and sometimes the sincere discussion works, i.e. “Grandparents, given that it’s my body and the tattoos are already here and not going anywhere, what are you hoping for when you comment on them that way? Do you really want our relationship to be about these tattoos you don’t like, or could we find a way to just be kind to each other?” 

10 “I’m scared my parents are gonna catch me stealing their Adderall.”

Well, yeah! Stealing another person’s prescription medication is illegal and wrong. It’s dangerous for you. It’s bad for them – your parents have that prescription for a reason, and if you’re stealing their pills they aren’t getting the medication they need. If you need evaluated for ADHD and to possibly be on your own medication, then ask your parents to help you do that. But stop stealing their drugs, please!

11 “Am I a selfish bitch for wanting more money?”

What if you could name the things you wanted without calling yourself mean names?

12 “Hinting that you want to get invited to someone’s house.”

Hinting doesn’t work. Try inviting these people to your house if you want to spend time with them, and if it really is about being inviting to something in particular just say it: “Next time you’re all playing badminton while wearing fancy hats, if you have room for me I’d love to join you.” Then withdraw. You’ve said your thing.

13 “Best response to someone who is seeking for a relationship from you.”

Hands down, the truth about what you want is probably best.

14 “Are grandmas always right about your gender?”

Not if their ideas about your gender conflict with what you know to be true about yourself!

15 “Why is my mom mad at me for taking a better job?”

IDK, but she’s not the one who has to work there, so your opinion is probably the important one here.

16 “How do you get your husband to set boundaries with his parents?”

He may or may not ever learn to do this and you can’t control that. So, you set boundaries with him, and with yourself. Basically “Husband, your relationship with your parents is yours to manage, but this is what I need from you to be happy and okay, so if your parents cross certain lines, I’m going to speak up and/or absent myself and let you deal with it.” 

17 “My boyfriend is always counseling me.” 

“Hey dude, if I want a therapist I’ll hire one.”

“Hey dude, if you want to be a therapist so bad, go be one!”

“Hey dude, even if you were a therapist, you couldn’t be my therapist, so stop.”

“Stop.”

18 “Best friend wants to be roommates but she’s too messy.”

Tell her “Friend, I love you so much, but I don’t want to cross those streams. I think we would stress each other out a lot if we lived together.” It doesn’t have to be a judgment on her, just, people will be happier living with people with similar definitions of clean when they are signing up to share housing. Knowing this about yourself is a good thing, decide accordingly.

19 “How to friendzone a guy you led on.” 

First step, RETHINK EVERYTHING ABOUT HOW YOU ARE DESCRIBING THIS. If we rewrite your whole question to “I wasn’t sure how I felt about this person, so I flirted with them, but now I’m pretty sure I just want to be friends, how do I let them know” we remove all the sexist assumptions that you owed your friend a certain outcome here.

Maybe try “I know we’ve been talking/flirting/kind of considering getting involved romantically, but I’m only interested in being friends.” 

Then, stop flirting (it’s the kind thing to do), and give the person a little space to process and decide if they want to be friends, too. You are not being mean when you do this, you are giving them true information that will help them make a good decision about what to do next. Friendship is not a consolation prize or a holding pen where we herd the people we don’t want to make out with, it’s its own valuable thing.

20 “What should I tell him I’m doing this weekend.”

A) Whatcha doing this weekend and B) Is it something you want him to know?

It’s the difference between “Oh, I’m busy with this and that, you know” and “I’ve got family coming into town, here is our detailed itinerary of fun!” and “I didn’t schedule anything in particular, why do you ask?” and “I’m going to the art museum on Friday, wanna join?” All are perfectly acceptable answers.

21 “Best response to ‘what are you looking for’ on Tinder.”

What are you looking for?

  • “I want to go to the comic book store and we’ll each pick out a comic for the other person.”
  • “I want to put on old soul records and make out a little bit but keep pants on at least the first time we meet up.”
  • “I want to come to your house and pretend that we’ll watch a movie.”
  • “I want to eat pancakes at midnight and talk about books.”
  • “I want to vanquish you at Scrabble.”
  • “I want to have one awesome night of no-strings-attached sex and then probably never see you again.”
  • “I want some cuddles and some good conversation but I’m not really about Teh Sex. Any fellow aces out here?”
  • “I want to throw a two person dance party in my basement, please bring disco ball.”
  • “I want to eat tacos and fuck.”
  • “I want to fall in love someday and not pretend that’s not what I’m after.”
  • “I want to play Dungeons & Dragons, but, you know, sexy.”
  • “I want to recapture a night from 1997, where we go see The English Patient and then close down one bar after another until we end up watching the sun rise from your car parked outside my house. I will provide costumes.”
  • “I need a cool extrovert to be my date to this swanky event and help me make small talk.”
  • “I need henchmen for my world domination plans, please submit application.”
  • “I’ve always wanted to build a pillow fort and then spend a whole Saturday in it in my pajamas. U up?”
  • “I signed up for this nonrefundable blacksmithing class with my ex and now I don’t want to go by myself. Any recently broken-up people out there want to learn a cool skill with me?”
  • “I never dated before and I want to try it out.”
  • “I’m in your city for the weekend for a work trip and I’d love it if someone who lives here would show me around. Can I buy you dinner at your favorite local spot?”
  • “Look this theater subscription isn’t going to use itself.”

What if instead of trying to find something that would be widely & generally appealing, you just got really specific about what you would actually like to do with a couple of free hours in the company of a new person?

22 “Can you pay someone in blood?”

No. Ew.

Wait. What did you buy on Vampire eBay?

 

 

 

 

 

 

Time for the monthly tradition where we answer the things people typed into search engines as if they are questions.

Before we get to it, it’s Pledge Drive Time! Twice a year, winter and summer, I interrupt our usual programming to remind folks that fun stuff like the Search Terms posts and the Friday short answers are funded by my kind and generous patrons and readers who support the site via PayPal and other ways. These donations allow me to keep the blog ad-free, invest substantial time in maintaining the community, reading the mailbox, and moderating comments, devote time to answering questions and writing new content, pay guest writers, and keep us functioning as an independent site. This year I’m trying to pull back on teaching and be a full-time writer, and your support is necessary and much appreciated for the care and feeding of me & my family. Please make a donation or become a patron if you can. Every little bit helps. (If you can’t afford to, don’t worry ’bout a thing, I’m glad you are here and reading.)

As is traditional, let’s begin with a song to set the mood. Lyrics here :

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Dear Captain Awkward,

I am a woman who met a guy online a month ago. He is really good looking, funny, shows interest in learning more about me (sadly uncommon!), and gets along with my friends. It hasn’t been perfect so far. Because I live in the city and he doesn’t, I have planned all our dates, so I don’t feel like I’m learning what he likes to do. Physically, he is moving much slower than I would prefer. He stares at me a lot when we are together and it makes me feel uncomfortable, like he is waiting to kiss me instead of enjoying time hanging out together.

We already had a talk about where things are going, and I told him his nervousness was making me feel uncomfortable and I wanted him to relax. He responded that it didn’t matter because I must like him since I’m hanging out with him. He also said he hasn’t gotten this far with a date in a long time, and he has “reasons” for being so awkward. He brings up his awkwardness quite frequently.

The real problem is that all this talk about being awkward makes me feel extremely angry and panicked. I find it very presumptuous that he assumes his “reasons” or trauma are worse than mine. That’s not how trauma works. I am also angry that he won’t be patient and give the relationship a chance to unfold. I feel like he is already emotionally committed, and that he doesn’t want to “screw it up.” It’s putting a lot of pressure on me. And, finally, the “I am really a nice guy” act sends up a big red flag for me.

Why am I so angry? How can I make him stop? Is our relationship doomed?

Thanks,
Triggered by Awkward Guy

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Hi Captain,

My question is not exactly high-stakes, but I’m having some anxiety about this situation all the same, and not sure what to do.

I (she/her) started using OkCupid recently, and a couple days ago, my coworker (he/him) who I don’t know well but see around often (we work at a very small company) sent me a message. I know it can be fun to send a couple silly messages back and forth when you see your friends on these sites without making it weird, but I don’t think this is that.

Anyway, if I see coworkers on dating sites, I think the polite thing to do is just ignore it and move along, so I was not super into the fact that this guy messaged me but I figured he was just being kind of socially obtuse. His message implied that he was going to ask me out “until he realized who I was,” which made me immediately uncomfortable. Dude, if you realized that, why did you message me anyway and tell me that?

I felt like ignoring him might make things weird at work, so I just messaged back noncommittally (like, “Ha, look who it is”), hoping I could move the conversation to peter out without making it awkward. However, things got awkward anyway, because coworker continued sending messages despite my polite attempts to disengage (“[Cool, unsolicited weekend plan you shared] sounds fun. Anyway, see you Monday!” …and then he’d send another message trying to continue the conversation.) I read and did not respond to the last message.

I’m sure I should communicate that I feel uncomfortable chatting with a coworker on a dating site, so do you have any scripts for that? Or would it be better to just block him and pretend it never happened? In hindsight, I feel like there are other things I could have said or done to end the conversation sooner, but that’s only now that I know I wasn’t able to end it without confrontation. It might be useful in general to know how to stop an inappropriate interaction like this in the future, so what would you have done?

Thanks!

OkAwkward

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Dearest Captain,

I’ve been dating a person for almost 3 months, and he is terrific and lovely. Sexy stuff is also ding ding ding jackpot!!!. I’m at the point where I would like to have a low-stress check-in about how we’re both feeling regarding exclusivity and commitment. I know we’re both currently not seeing anyone else. My general impression is that he’s interested in a relationship, but ‘impressions’ are not hard evidence and I just want to address it explicitly without my inner FEELINGS-VORTEX getting in the way.

I’m really struggling to find the right words to initiate this conversation, because everything that pops into my head has strong overtones of “PLEASE LOVE ME FOREVER” and “I’m putting all my hopes and dreams on you despite only having known you for 10 weeks or so”… and those are NOT the kinds of conversations I want to have. They’re definitely not representative of how I actually feel – it’s just that my anxious-attachment mechanism kicks into overdrive at the very thought of addressing it and everything starts to feel like much higher stakes than it really is.

I did some googling on “How to have a DTR conversation” or similar, and Captain, there is a universe of terrible advice out there. Of course, much of it is geared towards straight women, and either implies or outright says things like “Don’t be too pushy. Men don’t like to be rushed. Let him do the chasing.” DON’T STARTLE THE WILD MALE HUMAN. There’s a heck of a lot of cultural messaging to the effect that [in a heterosexual relationship] it is a woman’s role to push for commitment and that men dread this conversation, which makes me both extra nervous about it and also kind of resentful. I would like to be able to leave those feelings at the door when I bring it up, but I’m so lost for the right words to use that I just end up getting even more anxious, and then I don’t bring it up at all because I want to be coming from a place of curiosity and confidence, not from a place of fear.

I’m sure about this guy. He’s kind and responsible and we laugh together a lot and we are hella attracted to each other. I’ve felt a whole bunch of YES about him since we first met, and know that I know him a little better I feel totally sure that I want a committed relationship with him. It’s frustrating and embarrassing for me that I feel so lost as to how to bring this up. I know there’s no one-size-fits-all approach, but do you have any good scripts for having this kind of conversation? I think you’d be doing the world a great service by putting out a few (non-gendered) ways to check in with someone you’re dating about your hopes and feelings about the relationship.

Many thanks for all you do,

Looking For Words
(she/her/hers)

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