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Dating

Dear Captain,

I am a man and I have a problem: I’m a creep.

I’m 30 years old, and I haven’t had a whole lot of romantic experience. I’ve been shy my whole life and dealing with anxiety and depression since my teen years, so I haven’t put myself out there as much as I could have, and haven’t had the self-confidence to be a good prospect in the past.  My social skills have been getting better, and I’m getting treatment for my mental health issues.  I think I’m capable of dating now, and I’ve met a few interesting women to connect with in the last year or so.  These days, I even manage to gather up my courage and ask them out/confess my feelings.  However, I never to seem to get a straight “yes” or a “no”, and I end up responding in a bad way.  Some examples:

I met a friend-of-a-friend a few times before, and we had flirted with each other, so I was feeling confident about our connection.  Our group went to a party a while back, and I ended up asking to kiss her when we alone at one point.  She said “I don’t know” and it looked like she was nervous and didn’t know what to do.  I backed off physically, but I pressed the point: mostly questions in the “why not?” vein.  We parted without incident, but met back up at the end of the party (the group was riding back together).   For some reason, I tried to flirt some more, and I just ended up creeping her out.  I’ve had enough self-awareness to keep my distance ever since, though the damage has already been done.

Another scenario: I saw a woman on a regular basis at an activity.  I liked her, and told her so one day.  Confronted with the news, she became very awkward and didn’t give a clear verbal response (“oh…uh…”).  We ended up having a good conversation (about
everything else), but my declaration was left hanging.  Before I saw her again, I e-mailed her to ask to talk again—I had been flogging myself for not knowing what to say.  Her response was a clear “no”, and it was obvious that my e-mail had been unwelcome.  I was glad to get the straight-up answer, but I had to push her boundaries to get it.

There have also been a couple of recent instances where I’ve asked a woman out and didn’t take her “I can’t make it” as an “I don’t want to”, and have ended up pestering them again.

It’s clear that I’m establishing a disturbing pattern: I get interested in a woman; I make a move; she gives a non-committal response; I don’t take it as the brush-off it is and end up making unwelcome contact (i.e. asking for a date again, “but why?”, continuing to flirt beyond its welcome).  I know intellectually that getting a non-answer in these situations means “no”.  It’s also clear in retrospect that I should’ve just backed off in these cases, but I seem to panic in the moment and not act on that knowledge.  Through some combination of wishful thinking, inexperience and brain weasels, I’m pushing women’s boundaries and acting like a creep.

Any thoughts, Cap’n?  I feel so guilty about these instances, and I’ve reaped the personal consequences—burnt bridges and cold shoulders—but I’m still not getting it right.  How do I remember to bow out gracefully in such a moment?

– Don’t Wanna Be A Creep

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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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Hi Captain!

Many years ago, I was in love with a woman friend of mine, let’s call her P, and when I used my words, she told me that she didn’t feel the same way and was already in love with someone else (a mutual friend of ours, A). I was heart-broken and after about a year of being sad I resolved to move on and rebuild my life. I moved to a different country, went back to school to get an advanced degree and started a new job a year ago in my field. Although I wish I could have found someone else, I was mostly busy with my career and having been hurt + some personal issues about being a short guy (I was never bothered too much about my height before, but having been heart-broken seemed to have brought out my insecurities), I did not really pursue any relationships.

Now, as arranged marriages are customary in my culture, my parents want me to get married soon. At my age this is already considered very late in my culture and my parents tell me my prospects are thin and I should quickly settle for someone. While I like to think I don’t *have* to get married soon, or at all, I also feel very strongly that that’s not really an option for me. There’s enormous pressure in my society to settle down, I feel obligated to my parents and sometimes feel an arranged marriage is my best chance since dating is scary. Surely, my parents got married this way, as do lots of people in my culture, even some of my best friends, and are, by all appearances, on average, pretty happy.

Given this, how do I make the best of my situation, how do I learn to love someone who I barely know and who I may not be attracted to? When I talk to my friends, they always seem to have been into their prospective partners and vice-versa from the get go, they appear to not have had any major misgivings or spent any time thinking in terms like mine and in fact appear to have been excited and thrilled about starting a new life which is again, apparently, how their prospective partners also felt. When I listen to them, I think I want to feel that way too, feel genuinely thrilled and excited to find someone and get on with life and they advise me that “things just work out”. But I always end up concluding that either my outlook on life is different from theirs or that their personal situation isn’t like mine and so what worked for them may not work for me.

I also recently discovered that A and P had broken up and that A is now married to someone else(an arranged marriage no less!). I fantasize about getting back in touch with P and trying my luck again despite zero contact and no signs that P is even interested. I know that is just a fantasy but with the difficult choice of an arranged marriage, I keep thinking why not give it a shot.

I would greatly appreciate any advice on whether it’s even advisable to think about talking to P and if not, if you have any advice on how to go about being okay with an arranged marriage and learning to appreciate and love this other person who also may or may not be into me, given that putting off / not getting married isn’t an option.

Thanks,
Feeling Desperate

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Dear Captain Awkward,

I’m afraid I might be walking into an Alice situation (a la letter #247). My boyfriend’s family is very conservative and even though he is an adult, he not only lives with them (which is fine) but lives by their rules, curfews, and puts up with their interrogations over who he is spending time with, who his friends are, etc. They don’t know I exist, but he’ll be telling them within a month. He hasn’t so far because due to conservative culture reasons he can’t tell them he has a girlfriend, but rather that there is this girl (me) he wants to marry. And I’m terrified because they’re going to hate me (his mother especially) and I need scripts on how to deal with that when I meet them.

From everything he’s told me (and I take his word for it) I will be considered all wrong because I’m older than him, have been married before, am bisexual (here’s hoping his family needn’t find out, at least initially), am from a different culture (and don’t speak the language he speaks with his family, and his mother doesn’t speak English fluently), I’m not conservative and certainly don’t fit the mould of what a stereotypical wife would be like (I have no intention to just pop out babies, cook and clean, etc., which Boyfriend is fine with but his family won’t be), I’ve already vetoed the idea of us living with his family when we get married, and I’m expecting there to be body shaming.

Boyfriend has said that he expects his family’s displeasure about all of this to be voiced to him, and not to me and I know I can’t force them to like me. Boyfriend is also scared himself about their reaction to his upcoming conversation with them about wanting to marry me. I have tried to direct him to this site so he can read up some great advice about setting boundaries and making it clear what shit he will put up with and what he won’t, but he says that sort of thing is not done in his culture and apparently I just don’t understand (it’s true, I don’t), and while he sees that I’m trying to be helpful, it’s not helping because boundaries is just not the done thing.

How can I support him with this difficult conversation coming up for him (which will be more of an extended series of fights/arguments) while respecting his decision to not have me encourage him to set boundaries, while also being able to set boundaries myself? What am I meant to say to his family when I meet them (and yes, I’m trying to learn the language so I can at least exchange pleasantries with his mother)? (And yes, social anxiety and severe depression is making me overthink all of this, and yes, I am in therapy, but any scripts would help a lot!!).

Any help would be much appreciated,

Scared of future in-laws

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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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It’s time for the monthly ritual where I answer the questions that people typed into search engines to find this place.

1 “I have a crush on a guy who treats me badly.”

Crushes can be fun, but unlike what you’ve seen on Buffy The Vampire Slayer and every other show/movie/comic, love doesn’t turn assholes into acceptable boyfriends. My recommendation: Fantasize darkly about dirty-hot-hate-sex with him at your leisure, but save your actual affections and time outside your head for people who are kind to you.

Now more than ever we must hold the line and not waste our time with charismatic assholes.

spike

Admire my cheekbones from afar. Do not waste your precious life trying to turn me into an acceptable person to date.

2 “Talk about sexual relation first time.”

There is a site called Scarleteen. It is a national treasure, and while it was built so that teenagers could get non-judgmental, scientifically accurate, kind and sensitive sex advice, adults should read it, too. This topic is covered amply in their archives and forums.  The creator of the site, Heather Corinna, wrote a book called S.E.X. It’s great. They also have volunteers who answer questions confidentially.

While we’re on the topic, here are some other good books about sex:

Probably more recommendations in comments.

In the movies, sex just, like, happens. People stare at each other intensely and then grab each other and kiss and suddenly clothes are off and it’s all seamless and softly lit.

In real life, it’s important to talk about things with the person you plan to have sex with, especially when one or both of you is new at it. Everything from what consent looks like to “What are we gonna do about contraception (if that’s an issue in your pairing) and safer sex?” to  “I think I’d like it if we….” to “Definitely please do not ever….” to “That doesn’t feel good, please stop!” to “That feels really good!” Real life sex is awkward, and vulnerable, and that’s part of what’s great about it. Get thee to Scarleteen.

Happy talking! And everything that might come after!

3 “Working with the person you had an affair with now its awkward.”

Aw, buddy.

Without knowing the particulars (relative power structure in company, how it ended, what the feelings were and still are, how much time it’s been, did anybody know, what was the fallout, how much each person respectively likes/needs this particular job, etc.), some smart steps that you can control might be:

  • Keep your distance. You probably work in somewhat close quarters, which is how the whole thing started in the first place, and you can’t fix that or at least fix it right away, but you can start to mentally work on keeping your distance. Stop keeping track of the other person – their moods, quirks, likes, dislikes, what they ate today, who they talk to, where they go, reading their horoscope, etc. Stop fixating on them. Use the Bene Gesserit Litany Against Fear to distract yourself, if necessary, or just say to yourself , “We broke up, it’s not my business, la la la” when you find yourself getting obsessed.
  • Step up your professional game at work. Pay attention to the “little things,” like tidying your workspace, paying attention to dress & grooming, making sure you’re on time every day, being reliable & correct in your communications, keeping your boss updated on your projects, keeping small talk with coworkers very light and not revealing of personal life. I don’t think there is shame in crying it work – it’s a natural human response to stress and anger, and we shouldn’t be as dismissive of it as we are as a culture – but if you’re someone who is trying to keep an intra-office breakup private, try to do your crying in private. Put your best foot forward, even if you don’t feel like it right now. If you look to others like you have your shit together, it can sometimes help you keep your shit together.
  • Polish that resume. Look for another job, or an assignment in another department. I know, it’s not fair that you should have to leave your job, but it might be the simplest way to cut the cord of awkwardness. Join a networking organization for your profession if there is one. Make some new connections. Take a class and boost your skills in something. Maybe you feel like you can’t or don’t want to leave your job right now, but reminding yourself that you have options can’t hurt. Anything that reminds you of your own value is gonna feel good right now.
  • If there is stalking or harassing behavior of ANY kind, document & report it if you can. Whatever happened happened, but you don’t deserve to be terrorized or retaliated against professionally.
  • Give it time. Like the pain of all breakups, this too shall pass.

4How to break up your daughters gay relationship.”

Try these search terms instead:

“How do I show my daughter I love her and accept her?”

“How do I stop being a homophobic asshole?”

 Okay, speaking of affairs:

5 “What do you say to a married man’s wife who you have an affair with when she confronts you?”

Start with “I’m really, really sorry” and DO NOT try to justify or explain. The aggrieved spouse has probably saved up some things to say, so, just listen while they speak their piece. You don’t have to answer questions – “You should ask your spouse about that” is a good script if you start getting an interrogation, and if at some point you gotta end the conversation say, “I’m so sorry” again and refer the person back to their spouse, like, “I’m so sorry, I hear you, I know I hurt you. I don’t have answers for you, you should talk to (spouse) directly about this.

There’s nothing GOOD you can say, so, focus on not making it worse.

6 “Husband doesn’t believe his mother hates me.”

What if you said, “You don’t have to believe me, but when we’re around your mom and (this specific behavior) happens, I do need you to (defend me/shut it down/back me up/leave with me).

Focus not on the emotion (she hates you) but on the behaviors (the specific things she does that hurt your feelings or annoys you), and give him an idea of how he can best support you when those specific behaviors arrive. Choose your battles, and do what you can to minimize time with her. Annual Reminder: Nobody HAS to go home for the holidays.

7 “What to say in a Xmas card to a sister you did not talk with in five years.”

“Merry Christmas! I hope you’re doing well. Here’s [email/phone/the best way to contact me], can we catch up sometime in the new year?”

Take the pressure off to come up with something eloquent. This moment is literally what greeting cards are for – short, non-emotionally-charged communications. Give her a way to contact you and then leave it in her court. She’ll call/write or she won’t.

8 “Boyfriend does no chores and never wants to spend his free time with me.”

You could dump the boyfriend and get a cat. It wouldn’t do any chores, but least the cat would be cute and hang out with you sometimes.

male-model-cat-1

9 “Happy birthday to a friend you had a misunderstanding and now friends again.”

Say/Text/Facebook Wall: “Happy birthday!

Do you really want to rehash the misunderstanding? In someone’s birthday greeting? No. You don’t. Bake them a normal cake, not a shame-cake, and be glad that you mended fences about whatever it is.

10 “Boss upset I quit and I feel guilty.”

Your boss will get over it. Or they won’t, but you won’t work there anymore, so you don’t have to care.

11 “How to start the baby conversation with partner.”

“Partner, I’m thinking a lot about having a baby, and I’m pretty sure I want to start that process soon, with you. What do you think about that?”

Or, “I’m pretty sure I don’t ever want to have kids, so I wanted to see how you feel about that.”

Full disclosure, here’s how this conversation goes in my house:

We hang out with Commander Logic’s freaking adorable smart amazing children, aka, The Gateway Babies.

Spouse: “Someday, you know, my/our kids will….”

Me:

Repeat for a few weeks.

Me: “You keep mentioning these kids that will be doing stuff someday. Are these real kids or hypothetical kids?”

Spouse:

Me: “So, hypothetical. Ok.”

Spouse: (lots of stuff about parenthood and money and anxiety)

Me: (corresponding anxiety-brain-vomit)

Me: “If you really want kids, I’ll have your kids! I’ll have kids with you.”

Spouse: “That’s not exactly a ringing endorsement.”

Me: “It’s what I got. I can be happy either way.”

Both of Us:

Me: “Talk again in six months?”

Spouse: “Sure. Good talk, everyone.”

12 “What does it mean when a guy tells you ‘I cant ask you to wait for me’?”

It means, “don’t wait for me.” You have been or are about to be broken up with.

13 “A guy likes and comments on everything on Facebook stalker.”

You can: Set your posts using privacy filters so he can’t even see them.

You can: Unfriend his annoying ass.

You can: Block him so he can’t even know you exist on Facebook.

When/if…okay probably when…he contacts you through other channels to ask “Are you okay?” or “Did I do something wrong?” here’s your script:

“I wasn’t enjoying our online interactions so I stopped them.”

Monitoring a person’s every online breath is stifling and creepy. You don’t have to tutor him as to why.

14After party with my former students sex stories.

twitchy

No.

15 “My toddler seems lonely but I hate playdates and playgroups.”

From what I understand from my friends who are parents of young kids, EVERYONE HATES PLAYDATES. The other parents hate it as much as you do. They are going through the motions because they want their kids to have friends and be socialized. They are something you suck up and do until you find some other parents that you a) can stand to be around while the kids are very small and drop-off/self-play isn’t possible b) can trust with your kids as they get older so you can take turns dropping off the kids and getting a few hours to yourself.

Do you have a co-parent? Can they take some of the play-date and play-group pressure off? Like, if you both hate that, can you take turns sucking it up for the sake of the kid?

Can you find more structured stuff – craft things, a local children’s museum, story time at the library, swim/dance classes – that allow your kid to interact while you check out and read your phone in the bleachers?

You’re a good parent because you’re noticing your child’s loneliness. You’ll do the right thing. And this won’t be forever.

Hi Captain!

Longtime reader, very rare commenter but I think you generally give excellent advice so I’m giving it a shot. I’ll try to keep this relatively brief – I’m having an existential problem surrounding life milestones, etc. I’m 25 and have generally been pretty successful in my life – I’ve been academically successful, I have a law degree and a good job, and I have a really good group of friends, most of whom have been in my life for many years.

What I haven’t had is a whole lot of romantic relationships. This is generally fine with me. I really value my personal space and don’t generally crave the kind of constant companionship that comes with serious relationships. I’ve dumped people for “liking me too much” (ie, coming on too strong, wanting a kind of closeness I wasn’t comfortable with, etc). I’ve had one relationship that I would classify as “semi-serious” with a much older man that I met several years ago (we are still close and sometimes physically involved but not currently “in a relationship”). This relationship used to cause me a lot of emotional pain but I’m at peace with it now and don’t consider it a source of stress in my life. Additionally, I am kind of wary of men (I haven’t been raped or abused, fortunately, but have had the same experiences as a lot of women – sexual harassment, etc, lots of friends who are survivors) and am generally not one to give men “benefit of the doubt” when I’m uninterested or uncomfortable.

The problem is, certain family members seem to consistently insinuate that I need to “fix” my dating life. I’ve made the mistake of mentioning that I eventually might be interested in marriage/kids, which has apparently given these family members permission to ask about why I’m not dating, give unsolicited advice about my dating life or lack thereof, and critique the way I interact with men. These family members did not approve of my previous relationship (and I understand why, although it’s truly none of their business) and seem to be motivated by a desire to see me “move on” from it. I always feel like they’re trying to tell me there’s something wrong with me for not being all that interested in dating; I’m also a pretty private person and don’t tend to talk about people I casually date/am interested in.

I’m at an age where a lot of my friends are in serious relationships and some are married, and the pressure is starting to get to me. Eventually, a relationship would be nice. I love kids and would like to have some of my own someday. But I need to do it on my own timeline, when I’m comfortable, when I figure out what I want and what I need. I’m not even 100% sure that I’m not bisexual. Scripts like “I don’t want to talk about my dating life/relationships” have only been interpreted as an invitation to “push” harder from these family members, and this lack of respect for my boundaries seems to be fraying my familial relationships that are really important to me. I want to be close with my family but I’m also an adult and need people to mind their own business, and I don’t know what to do. Any advice?

Best,

Single and Stressed (she/her)

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