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Captain Awkward’s Dating Guide for Geeks

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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Hi Captain!

My problem is one that I imagine is very, very common, but I’ll start with a little background on my specific situation.

I recently started going to therapy for some pretty serious self esteem issues that had led to me isolating myself for a long time. Up until this year I hadn’t been to a non-family social event – including just one-on-one hangs – in over five years (and even before that it was pretty rare).I’ve made a lot of progress over the last few months; I have a few good friends that I can go out with and all in all, I have learned how to get better about relentlessly judging myself during and after every social interaction.

But even after all this (successful!) work, there’s one aspect that I just can’t seem to crack, even with my wonderful therapist, which is the possibility of a romantic relationship. It has been ten years since my last relationship (I’m in my early30s) and I haven’t been on so much as a date since then. While I was in my hermit state I vacillated between “I don’t really want a partner anyway” (a big fat lie) and “You’re not worth a relationship.” Basically the idea of being involved with someone in a romantic way seemed to be something that just wasn’t in the cards for me, ever. I always pictured myself alone.

Now, though, that I’ve started being around people socially, it’s starting to seem…not so insane. Like maybe it’s not out of the realm of possibility anymore, at least not when I think about it in an abstract way. But when it comes to a practical way – joining a dating site, talking to guys at social events, whatever – I can’t seem to break that bubble of “Why even bother? Who would want to be with you?” Even just writing this part of the letter made me feel embarrassed and silly.

There’s one important thing at play here that I haven’t mentioned yet: I’m fat. [details of weight redacted by Captain Awkward, per the site policies] I just can’t stop thinking of my weight (and looks in general, to a lesser extent) as my #1 defining characteristic.

It’s pretty easy to draw a straight line directly from media portrayals to my issues in this area. A fat girl talking about sex is almost always a punch line, a character for everyone else to make “ew, gross” faces about. Despite intellectually knowing better, I’ve internalized this message. For instance, occasionally I’ll use Tinder when I’m bored or feeling optimistic about the future (but mostly bored), and one time I ran across a co-worker. What should have been a “haha isn’t this awkward” moment sent me into a complete meltdown. I was *mortified* that this co-worker might think that…I don’t know, that I thought someone would be attracted to me? It was ages (like, literally a year and a half) before I could be around this extremely nice co-worker without wanting to crawl under the table and die. I couldn’t even talk to him.

So that’s basically where I am. This feeling that, no matter how funny or kind or interesting I am inside, it doesn’t even matter because my outside is so unappealing. I get so sad thinking about how no one will ever look at me and think, “Oh, she’s pretty, I’d like to get to know her”.

How can I start to escape the “overweight=unfuckable, unfuckable=unlovable” cycle?

-Want To Make The Rockin’ World Go ‘Round (She)

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Ahoy there Captain!

My boyfriend, who I met online through a mutual friend, and I have been dating for about two years now. When we first started talking online, we lived on opposite sides of the country and were in a long distance relationship for over a year before I decided to move to the same city as him. (We each have our own place, though.) Due to his job he was unable to move to my city, so I decided to be the one to move. I had fallen out of touch with many of my friends from back home for varying reasons and had a job that was just okay, so aside from the fact that it was expensive, the move wasn’t too hard on me.

Now, about eight months after moving here, I am falling out of love with my boyfriend. He hasn’t done anything wrong – in fact, in many aspects, he’s a fantastic partner. But the days are fewer and more far between that I can see myself having a future with him. I rarely feel any sexual attraction towards him, and more and more things about the relationship are becoming things that I don’t see myself being 100% cool with in the future. (He’s not really excited about the prospect of kids, he’s not close with his family, we have incompatible sex drives, etc.)

I’ve talked with him briefly about how I don’t feel totally satisfied with the relationship, but with the holiday season in full swing as well as a vacation we’re taking together in the near future, we decided to push things under the rug. However, at this point I’m feeling pretty confident that this relationship isn’t meant to last.

However, my fear (and by extension, the underlying question of this email) is that without him in my life, I am completely alone. I have no friends here, and all of my friends that I do have are either in a mutual friend group with my boyfriend or live very far away. I’m worried that I will essentially hole up in my apartment and never leave because I have no one with whom to do activities. (As a sufferer of depression, this fear is only increased.) I don’t like the idea of spending that much of my time alone. And, of course, while I do not feel this relationship is working out, I do care for my boyfriend a lot and would miss him so, so much. (I would love to stay friends, as he is genuinely one of the best friends I’ve ever had, but I’m not sure if that’s possible.)

Do you have any advice on how to go about this? I’m not even sure how to break up with him, let alone what either of us will do afterwards. It’s funny- I can’t see him being my partner forever, but I also can’t imagine my life without his friendship.

Thanks a bunch!
-Moving on after moving away
(She/her pronouns)

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Dear Captain Awkward:

A girl I’ve been seeing for 5 weeks broke up with me and it hit me really hard. It took me a night to realize that I had attributed a lot of emotional weight to staying over at her place on week 4, when she asked me to come over and stay the night . So when we had the break up talk the week after that, I felt completely blindsided.

In my mind, staying the night means we are Officially In A Relationship. I was already imagining meeting her friends and hopefully eventually her family, stuff like that. In the days following that night, she invited me to a gathering with her friends and also to a dinner her friend invited both of us to, so it seemed like my expectations of what that night meant were holding true; up to that point I hadn’t met any of her friends. And then a week later she wanted to break up.

I told her my feelings about that night during the breakup, and her response was the typical “you built up too much of this relationship too fast, maybe slow it down in the future.” But I really don’t think I can change how I feel about staying the night with someone. Based on talking to some friends, it seems like people my age don’t attach nearly as much weight to this as I do, as it’s just one of Those Things You Do in a new relationship. Is there anything I can do to resolve this disparity in the future when dating someone new?

Basic background: I’m 28 years old and I didn’t start dating until I was 25. The longest relationship I’ve been in was 6 weeks. I’ve read about attachment patterns in adults and I solidly fall into the anxious-preoccupied model.

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It’s been a long time since we’ve looked into the abyssthe internet’s unfiltered Id… the words that people type into their search engine windows in order to find this place. Good news, Patreon contributors met the first monthly goal, and this will be coming back as a monthly feature. Shall we dance?

1. “Colleagues surprised I got promoted.”

And they point out their surprise? To you? Depending on my comfort level & closeness with the people in question and the likelihood that they’d have the grace to be embarrassed, I might say something like “Thanks for that astounding vote of confidence, Marian!” to help everyone laugh off the moment. I might also call no attention to it and pretend I didn’t notice, based on the fact that sometimes people have weird reactions to things when they first find out about them and do better when their first reaction can be private.

Now, if they keep bringing it up after that first announcement, like, “I was so surprised they promoted you and not Andy…” – it’s time for a wicked smile and “And yet…here we are!” (+ subject change).

2. “Can I ask neighbours not to be on my drive.”

Yes? “Please don’t use my drive, thank you.

3. “My mother died without resolving our strained relationship or saying thank you.”

We all die in the middle of something unfinished.That SUCKS and I’m sorry for the loss of your mom and for the loss of the chance to make things right between you. It sucks to be grieving someone when you’re bouncing back and forth between grief and anger and regret.

I hope you will honor your mother’s memory and your own experiences with your mom (the ones that made you need to keep your distance) someday when some more time has gone by. Write her a letter of all the things you wanted to say to her, but didn’t. Write the letter back to yourself that you wish that she would send you, the one where she says, “Thank you” and “I’m sorry” and “I understand.

Be kind to yourself.

4. “Why would a man tell you he will take you out for coffee once in a while, even after breaking up?”

Maybe this man has some idea that you’ll still be friendly. Only he knows for sure, so before you say yes you might ask him: “Hey, was there something in particular you wanted to talk about over coffee?”

Before you go, ask yourself:

Do you want to go out for coffee?

Do you want to stay in contact, or would you benefit from a clean break?

Do you want to go even if it doesn’t really mean anything special about your future together?

5. “People who care about grad school too much.”

Duuuuuuuude. Seriously. What is it with grad school, being all expensive and intense and competitive and interesting and stuff.

(I have no good answer, sorry. Grad school: It’s absorbing.)

6. “She says, ‘Not now, sorry’ when I want to talk with her.”

My best guess is that she is busy and doesn’t want to talk right now.

Try saying, “Ok, let me know when it’s a good time” and then going and doing something else with your time for a while.

In a good [romance][friendship][artistic collaboration] she’ll come find you when she’s ready.

7. “My brother is an insufferable ass.”

You can’t choose your family. Can you limit the amount of time you spend in his company?

8. “If my boyfriend forces me to change my appearance”

Is this one of those fill-in-the-blank scenarios?

“If my boyfriend forces me to change my appearance, and it is not a matter of life and death because we are on the run from an international spy ring, then I should dump him for being a controlling jerk!”

People who “force” you to change important things about yourself are not on your side, Young Googler. Please love yourself enough to get away from this person.

9. “Why is my boyfriend really aggressive about me wearing makeup?”

The simplest explanation is that he does it because he is a controlling asswipe. See #8. He is literally trying to control your face. 

10. If a family member shuns you, do they ever think of you?

Maybe? Sometimes? Without action on their part, it’s hard to know.

11. “I found my grandmother’s sex toys.”

Yes! GET IT, GRANNY!

My best suggestion is: Put them back where you found them and act the way you’d like Nana to act if she stumbled across your sex toys (i.e. “quiet” & ” discreet”).

12. “‘Sorry I can’t date you’ message.”

I like replacing “can’t” with “don’t want to” or “am not interested,” if you feel safe to do so. “Can’t” implies circumstances beyond your control, like, “I would totally date you, but this tornado just spirited me away to the land of Oz, so I can’t.” That little window of ambiguity can send a persistent lover into a tizzy of looking for ruby slippers that will click you back to Kansas when really you just want them to leave you in this Technicolor world where it’s not the Great Depression. Whereas, “It’s nice of you to ask, but I am not interested in dating you” is clearer and more specific.

13. “Are all bad girls confident?”

Marie Claire’s former pillock-in-chief Rich would have it so. I need a better definition of terms. What is a ‘bad girl,’ exactly?

14. “How many times should I invite myself to stay as a house guest?”

This is my personal house-guesting code as a 42-year-old white American lady with a job. It does not have to be your personal house-guesting code.

With a close friend or family member,

Where I have a good history of reciprocity,

And I trust them to say an honest “no” if it’s not a good time or whatever,

And the dates of my travel are pretty well-defined (nobody likes “sometime” hanging over their head) and short (1 night – a few days);

…I may ask once or twice or every now and again. More likely when I know that the hosts have a guest room and a habit of saying “Please come visit, we have a guest room and we’d love for you to stay with us!,” in which case, they have invited me and “inviting myself” is more about suggesting a specific time. Much less likely when there is no guest room or guest bed and I’d be taking up someone’s main living space. Not at all likely when the prospective hosts are brand-new parents of a baby or enmeshed in other big deal life stuff. Definitely not if a suggestion of staying there is met with any hesitation; one may askIs it okay if I stay in your guest room for a few days?” but one must not try to convince the hosts.

This was all more fungible when I was 25 and used words like “crash” and traveled more internationally and AirBnB did not exist.

15. “How to ask friends not to invite themselves over?”

“Hey, friend, I love your company, but when it comes to my space, can you wait until I invite you over? Thank you.”

16. “I don’t want to be friends with ex-boyfriends.”

You don’t have to be!

17. “A message to write to a friend to tell some one they are of value to you even if they have gone broke.”

“Hello, friend, I know times are really hard right now. I just wanted to say that you are important to me and I’m hoping things get better for you. Can I fix you dinner sometime soon? I’d love to see your face.” 

18. “What is Captain in sex?”

If you’re lucky, there’s a recorder solo.

19. “Should teenage boys have sex toys?”

I’m neither a parent nor a legal expert, but my instincts say, “Why the hell shouldn’t all teenagers have access to information & resources to make themselves feel really really good in their own company?” I wish to hell I had grown up with Scarleteen and a waterproof, adjustable-speed vibrator.

20. “Do therapists want to hear how their former patients are doing?”

People in the helping professions sow a lot of seeds without expecting to see the blossoms, so, I say “yes” if you had a good relationship and the information is conveyed in a medium that doesn’t demand work from them. Think of it the way you’d write to a former teacher you wanted to thank in a short note, like, “Dear Therapist, I just wanted to let you know that things are going better at work thanks to your suggestions for managing my time and anxiety better. I hope all is well with you, thank you again for your help. Sincerely, Your former patient.” If you find yourself generating paragraph upon paragraph of text, maybe make an appointment?

21. “Stop meddling and being a matchmaker!” 

Yeah, knock it off, Emma! 

22. “Me and boyfriend break up because we never have sex.”

Breakups are HARD, even when they are the right thing to do. I hope you are both happier with a little time and distance, and may your next partner(s) be more compatible with you in that way.

23. “Should it bother me that my husband wants me to party with alcohol & cocaine knowing I have seizures and interactions with medications could be harmful?”

I find it useful to replace the word “should” in talks I have with myself. When we’re talking about feelings or big decisions, what “should” happen is not so helpful. The better question is “what IS happening?”

“Should it bother you…”

==>

DOES it bother you? It sounds like it bothers you. (It bothers me!) And, since you are the sole boss of what substances you put in your body, you are the sole decider of what risks are unacceptable for you. “Husband, I don’t want to ‘party’ with you. I don’t want to have a seizure or a bad interaction with my meds. Please stop asking me.”

24. “My roommate leaves the bathroom door open when he goes to the bathroom and showers.”

“Dude, close the door!” (+ open the window!)

 25. How to get your boyfriend to look after himself?

Any answer I give is going to generate an automatic “But it’s more complicated than that!” or “But I love him!” response, and rightly so, but I’m going to talk to my younger right now and let everyone listen in. If it’s not applicable then it’s not applicable.

Hey, Young Jennifer, I’m so sorry, the Time Machine did not get me back here in time to stop you from falling in love with [Hot But Troubled Boy]. I had the dial set for 1990, which is why I have all these catalogues for women’s colleges and a bass guitar in here with me, but I can see that I’m a couple years late.

I know you love Boy. His skin feels like magic and when you touch each other it feels like the microscopic space between you is filled with stardust. He smells like two angels fucking. You can stay up all night talking and fixing the world together. You are unstoppable…except for when he is very stoppable.

Boy has a condition called depression. You have it, too, and you should go and get checked out for that. Where I come from you didn’t figure that out for another 5-7 years, and I can’t help but wonder what would be different for me/us if you knew. Depression doesn’t mean you’re unloveable, it just means that it can take medical help and concentrated effort to manage the condition. When Boy hates himself, and stops going to work or class or washing his clothes or wanting to do anything with you, when he has mood swings and gets dark and mean, when he tells you that he doesn’t deserve you and wants you to go away, and then the next day tells you that he’ll die if you leave him,  it’s at least partly a manifestation of an illness. It’s not your fault, it’s not something you are doing wrong or not doing enough of. What that also means is that you cannot love him out of it. You can’t fix him or fix it for him. He’s got to do it himself.

What I know now that you don’t know is that the time you are spending, tidying his space for him, worrying about him, talking to your friends about what to do about him, trying to coax him to eat or shower or go see a movie with you, wondering what he’s thinking about, making sure you always look pretty when you see him, keeping track of his schedule and his deadlines, processing the stuff he says to you in and out of his mood swings, taking care of him, trying to lay your love and your body down into all his cracks and fill them, time spent biting your tongue not wanting to make him sad or angry…this is time that you will never get back. You are stealing these years from yourself and offering them up to him, to no one’s benefit.

I know, you love him. I know.

And I have unfair knowledge, because I know stuff that you can’t know now, that maybe you wouldn’t have ever learned if you didn’t try and fail at this.

But I’m from the future, and if I could tell you what to do right now I’d tell you to have one conversation with him where you ask him to seek help for his troubles and to start being nicer to you. If he does? Great, maybe you can have that love story you’re so sure this is going to be. If he won’t? Especially the part about being nice to you? Then I’d tell you to bail. It’s too late for the women’s colleges, but it’s not too late for the bass. Take it, find some other awesome women, start a terrible punk band, and use all the painful things he’s said to you as material for lyrics. Hold out for someone who is always kind to you, someone who doesn’t need to be fixed or parented.

P.S. In 1997, when your friend I. offers you a chance to work at her internet startup but you’re going to take the job at the non-profit instead? WORK FOR I, FOOL. She’s gonna sell that thing to Yahoo right before the crash in 2000, and you can donate your millions of dollars to the non-profit.

This is Captain Awkward Dot Com Pledge Drive Week, as you know. Ways to contribute:

  • You can become a patron at Patreon. At the next funding goal, I release an e-book of columns once every year, free to patrons, a few $ to download for non-patrons. When/if we hit $2000/month, the blog goes ad-free. 
  • Monthly contributions not your thing? Paypal Cash.me and Dwolla also work. Whatever’s convenient for you!

Thank you so much for reading and for your generosity. It really makes a material difference in my life.

 

 

Dear Captain Awkward,

I couldn’t find anything like this in your archives, so I hope you don’t mind me asking for advice.

I’m a 23 year old woman and I’ve never been in a relationship. It just doesn’t particularly interest me, and I identify as an aro-ace and I feel satisfied by all my platonic relationships. I have dated in the past, which has clued me in to things I like and don’t like, and I’ve also come to realise that dating people I don’t know makes me really uncomfortable with the thought that they will want things I don’t.

During school, my friends told me that a guy at a party had been hardcore flirting with me and I hadn’t noticed. I’ve been messaging him on and off since and we’ve gone on two dates, and I don’t know him well enough to want to go on more – I want to know him as a friend before we try more dates. The problem is, one of my friends is meddling to try and push me into a relationship with him, and I just want to run the other way. Despite not hanging out in five years of school, she’s asked me twice in two weeks to hang out and if I decline to save money, changes plans conveniently so that I don’t have to pay anything. I know she’s meddling, and another friend has admitted as such. All she’s doing is making me want to duck my head and hide – the more she pushes, the less I want to know this guy at all.

I don’t know how to tell this guy that I want to know him as a friend before we progress without hurting his feelings, and I really need to tell my friend to stop meddling because it makes me really anxious and uncomfortable, but I have no idea how. Do you have any advice or scripts that might help?

Thanks,
Happily Single and Being Pressured

Dear Happily Single:

Be blunt and let them know where you stand. It’s actually the respectful, friendly thing to do. You can do it!

“Friend, stop meddling. I will work things out with this guy in my own way and at my own pace. You’re driving me bonkers right now and making me feel pressured and annoyed. Knock it off!”

“Guy, I like hanging out with you and I’d like to maybe be friends. I don’t think I want to go on any more DATE-dates for the time being, though I will let you know if that changes. Is that cool?” 

“I’m happy being single.” (Repeat as necessary, to the point where the conversations become very boring because you default to saying this every time the topic comes up). “But won’t you give him a chance?” “I’m happy being single.” “But he was flirting with you!” “Cool. I’m happy being single.” “I just want you to be happy.” “Good! I’m happy being single.” “But I thought you liiiiiked me.” “I do like you as a friend. I’m happy being single.” “I just want to help you.” “But I don’t want help. I’m happy being single.”

You already know what I’m gonna say: I’m happy being single.

Guy and Friend(s) will feel whatever they feel. Maybe Guy won’t be interested in hanging out just as friends. Maybe Friend(s) will deny their meddling or be offended that you don’t want them to do more of it and be miffed for a while. Maybe they will get it and apologize and stop pressuring you. You can’t magically prevent people from doing stuff that annoys you, but you can have a conversation where you let them know how you feel about it. Stop silently accepting their annoying behavior. You are not “being mean” or “causing trouble” by stating your needs and boundaries. 

You got this!

 

 

Dear Captain Awkward,

Met this girl through her uncle, have known her for
Over 20 months, we’ve met a couple of times, nothing much happened, but used to keep ourselves updated over texts, she asked me out for dinner or lunch a couple of times, I had important things to address at that point of time, nor was I sure about my feelings towards her, it’s been six months since she moved to Australia for her education, that’s when I realised she’s the one, i’m not active much on social media, don’t keep my profile updated, and I did confess to her about me liking her, she said it was overwhelming but she isn’t into anyone now and wishes to focus on her career and has a lot going on her plate now, and since then she says she’s busy with all her things back there, but i see she’s got a pretty happening life making new guy friends and isn’t as busy as she’d told me that she is, with all her assessments and assignments, according to her social media updates, when I’m back here in India, wasting my time thinking about her, she’s back in town but hasn’t kept me informed, got to know this through social media too, and I have no idea what she thinks about me, because the moment I told her I like her, she tried avoiding, when I stopped completely she checked on me a couple of times by leaving me texts and when I replied acting like nothing ever happened, I feel she’s brushed me off, saying she’s got her semester exams going, and is currently in town meeting all her friends here, and we’re twenty years old, please do not ask me to refer a forum! 😛 Thank you.

Regards,
R.

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