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Captain Awkward’s Dating Guide for Geeks

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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Hi Captain Awkward!

I’m in need of your spot-on dating advice and I’ll get right to it. This evening, I went on my fourth online dating website “date” (which usually is just find a place to chat for a couple hours) and, like the previous three dates, I have realized that the girl that I’ve chatted with for a while online just doesn’t seem that interested in me. (She still could be, but I just got back from the date and I think it’s smart to take a break from texting – don’t want to overwhelm her/appear clingy.) One of the main indicators that she just wasn’t interested in me was the fact that she wasn’t really trying to establish any physical contact. Being an introverted geek, where dating doesn’t come naturally to me, I’ve read about “breaking the touch barrier” and trying to create a (even slight) sense of intimacy on the first date. No, this doesn’t necessarily mean “make out” on the first date, but I always introduce myself with a hug; establish eye contact whenever possible; and give occasional friendly taps on the shoulder to establish a welcoming persona. I’m really trying my best to be better at dating but I’ve realized my problem is that I have a hard time creating intimacy on the first date and appearing like a desirable guy to my date. In short, I get the sense that even though we agree on a lot of topics and hobbies, I can never get my dates to “want” me like some other suave guys can do. Also, in between chatting about our hobbies, where we come from, what we like, etc., I tend to have a few awkward pauses during my dates. I’ve reasoned that it’s best to ALLOW these awkward pauses to occur, even if we’re just awkwardly sitting in silence, because a) You want to give her time to think/process what’s happening and b) you don’t want to appear like the blabbermouth who doesn’t know when to shut up. So I allow awkward pauses to happen, even if they sometimes seem to kill the mood. Should I do something differently there?

Sincerely,
Padawaan Dater

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Hi Captain,

I’ve dug through your archives but haven’t seen anything specifically on this topic–apologies if I’ve overlooked something–but I’m wondering what advice you have to give for partners who make the decision to work through a mistake and rebuild confidence in each other.

Long story short: I’ve been dating my partner for a few months, but we’ve been very close & important presences in each others’ lives as friends for about 2 years before we began dating. About a month ago he made a very stupid, but not unforgivable, mistake involving an ex of his as they tested the waters to see if they could function as friends (turns out, no, they can’t). He has been nothing but honest and forthright about it since it happened, and although we were both unsure before this happened as to how seriously we could commit to each other (eg: neither of us felt comfortable using boyfriend or girlfriend as a term then or now, but agreed what we are is much more than just “seeing each other.” It’s somewhere in between), since this all went down we have both doubled down on supporting and prioritizing each other as a couple.

We are also both going through the joyful process of cutting an ex out of our lives, because in both cases they love us more than we can ever love them & cannot healthily function in a 100% platonic environment with us at this moment. So space and time is in order for healing. Which is giving us both anxiety (both for ourselves and for each other) and making us very sad. We are trying to balance that line of support–historically we have leaned on each other during times of anxiety and stress–and also take into play your “not my circus, not my monkeys” rule to manage our anxieties and control issues (eg: I think he’s taking the “typing http://www.google.com with one finger when he could just use Chrome” route to cutting his ex out, and desperately want to tell him to metaphorically scooch over so I can do it for him, but his path cannot be my problem so long as he handles it in a way that doesn’t hurt me).

We both lead full lives with hobbies that we share, hobbies we don’t share, friends we share, friends we don’t share. I’m doubling down on the self-care and detachment (from trying to control the way he handles his issue with his ex) and he is staying present and vigilant about executing his goals while also practicing self-care. Even still, it’s difficult. Now that the holidays are over it has been particularly hard not to ruminate, and while I’m journaling and working through several aspects of this within myself, I also feel the need for support. (Just today I emailed my old therapist to see if she takes my new insurance) After keeping it to myself for a couple days I finally confessed to him that I’m still struggling and feeling sad/hurt/anxious. He said he is too, but that we’re living with it as we work through it, which feels very accurate. And then I felt guilty for bringing it up at all, which is a whole different barrel of social conditioning worms (I am female, partner is male–late twenties, early thirties respectively).

I guess my question is: we’ve decided to stick it out and work through a difficult time… now what? Both of our ingrained reactions are to cut and run when things get messy, but we want to try (with the understanding that it could fail anyway) and I’m feeling a little lost for what to do. Is this just how it is?

Sincerely,
Longing For A Reset Button, Would Be Happy With A User Manual

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Dearest Captain,

I have had a rough few months in which I have temporarily moved home to deal with a highly stressful situation. The crisis itself has largely passed, but I’ve decided to stick around for the holidays, since I do love my family and they don’t seem to mind me crashing with them for a while longer.

The most prominent issue in my life right now is with one of my new friends in my new state. He’s a nice guy and all, but he’s kind of…irritating. I didn’t say much to him before I left to go back home, but he knows that there was an emergency and that I’d be out of town indefinitely. Since I left, he hasn’t stopped pestering me to ask me how I’m doing (crisis situation, wtf does he think?) and sending me pictures and motivational quotes in the name of trying to cheer me up at least once a week. The latest was a picture of a rainbow intended to “Brighton [sic] your day!”

I’m aware that there are far worse problems to have, but he’s driving me nuts. I haven’t responded to him in nearly two months because of other priorities, including not wanting to get sucked into a drawn-out conversation I don’t have the energy for, and he is damn near impossible to shake once he’s got any sort of handhold. However, he’s also damn near impossible to shake even after two months of silence on my part, go figure.

I feel like I’m on the other side of Letter 366, where I’ve got the avoidant attachment style, and the harder people cling, the harder I push them away. I consider myself very independent, and I know that’s feeding into this as well…if I’m going to be cheered up or have my day brightened, I want it to come from within, when I’m ready to start feeling better on my own. My close friends know to let me wallow in self-pity until I arrive at a more balanced frame of mind on my own.

Is it all right to tell him, “Don’t call me, I’ll call you?” I’m not necessarily sure I want to cut him out of my life entirely, but I am sure that I need him to drop the contact attempts way back and make the ones he does send less saccharinely feel-good.

-Let Me Mope in Peace

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The post title was the subject of the email exactly as it came to my inbox. That will be important later.

Hey there Captain,

I recently moved to a job that not only frees up more time to focus on schooling, but pays better. On the last day at my previous job, a girl I’d occasionally worked with and spoken with in the breakroom, asked for my number.

If her interest wasn’t obvious enough, as I walked out the door for the final time, her question was whether I had a girlfriend. I told her no, and to my amusement, her reply was that she’d text me. Needless to say, I got a text bright and early the next morning and we’ve been texting a bit.

She’s nice and I get along well with her, but I’m unsure about making the choice to date her. There are a few things I see as obstacles, but can be worked through.

She’s the daughter of my previous manager. Introductions as a boyfriend would be awkward because my manager didn’t want me to leave. I worked hard, kept a positive outlook, and somehow managed to get along with even the prickly people there. I lit up many people in that glum environment.

While texting, she obviously wanted to get to know me better, so I took the lead, organized a meetup, and we had fun, went for coffee, and wandered around the mall.

It was a great chance to get a feel for her personality, lifestyle, relationships, and maturity. When I asked her what she enjoys doing, she said that she didn’t really have any hobbies, but that she enjoys hanging out.

During the meetup, she spoke mostly about how she doesn’t like work, her parents are always mad at her, her exes (about two or three by how she spoke about them), and her life in general. After the meetup, she told me she had fun and wants to meetup again next week (the next free day she has).

Clearly she enjoyed my company if she already wants to hang out again. I asked what she wanted to do, and she said “I don’t know, I’m good with anything”. This bothered me somewhat, but I’m a big boy, not everyone knows how to be assertive.

When I asked whether she’s doing post-secondary, her answer was the generic “I hated school, so maybe I’ll become a cosmetician”. She agrees with whatever I say and doesn’t have a lot to say about her day, goals, or hobbies. That bothered me more deeply. I’m easygoing, so I spent time reflecting on why this information bothered me.

I have my life together. I’ve got a great part-time job to cover costs, university and my budget balances at the end of the day. I pursue hobbies such as photography, programming, hiking, and cooking. I’m on great terms with my family. I know myself well and what I want in a companion. This girl is wonderful, but it seems she dates as a form of entertainment; escape from her life. I date for a strong equal to share my interesting life with, and I’m not seeing a lot of that in her.

I’m not interested in being a crutch and I can’t save her from a boring life. If there’s a way for her to grow up and not rely on me to fill up her open schedule, I’m open to sharing a life with her. Although she’s my age (19), I don’t think she’s at the point where I can tell her this without grievously wounding her undeveloped ego, especially given how she admires me.

My first relationship (a different girl), about a year ago, ended because both of us had been insecure. Since then, I worked at self-improvement, and I’ve honestly been impressed with my progress. I’m a much more confident and relaxed person than I was.

I know myself well enough to know conversation is important to me. I’d feel lonelier in a relationship than alone if the other person had nothing interesting to talk about, AKA, their own life. I’m looking for a healthy relationship where our worlds don’t revolve around each other, but where we know there’s respite in each other’s company.

How can I kindly tell her that she’s wonderful and brave, but not ready to be the female lead in my story?

Signed,
Casting a Female Lead

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