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Captain Awkward’s Dating Guide for Geeks

Hi

I am a man in the late twenties, who have zero dating experience.

I have recently met an insurance agent on the street who approached me to get my contact. Even though I mentioned to her that I already have my insurance adequately covered and personal agent whom I trust a lot and thus is unlikely to be getting anything else insurance-related from her, she remained friendly and said that she would still like to meet up for coffee one day and thus I gave her my contact eventually.

I have to admit that I was rather apprehensive at first since I was familiar with the insurance agents’ ‘modus operandi’. They would generally position themselves along the busier walkways and utilise a ‘throw everything at the wall, some will eventually stick’ approach by striking up a conversation beginning with a survey to get a brief outlook of your financial status and then arranging a meetup so as to perform a personal review and then to persuade the other person to take up policies from them. This is so as they are generally paid based via commission and have a target to hit every month.

As such, knowing myself that I would not be taking up any policies for certain and so as not to waste the other person’s time, I would try to avoid them or just decline politely. As in this case I was already upfront with her, I thought that there’s no harm meeting up just on a friendly pretext if she wants to.

Subsequently, we met up twice over lunch. During the first meet-up, we chatted a bit and eventually, she turned the conversation towards my financial position and on giving a second opinion. Once again, I reiterated my position (especially in addition to the fact that I’m currently taking part-time studies and am really strapped on cash).

Still, the whole lunch appear to go over quite well and I was keen on meeting up with her again. I asked her out over text and she agreed. The second time, we just chatted about stuff in general and did not mention anything insurance related at all.

I thought that things were going well, however, my past two attempts at getting to meet her up again have been faced with her attempting to postponing by mentioning that she is really busy with work. In our last correspondence, she even mentioned that unless it is to meet up for ‘business’ even though she ended with a ‘just kidding’.

Should I just forget about her and move on? I should mention that I’m a very introverted person in general and rather bad at reading social cues. Thus I have a hunch that my optimism was misplaced and that she actually just viewed me as a potential customer.

Thanks!

Head says yes but heart says no.

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Hi,

I’m very attracted to a man I see in my local supermarket, I’ve seen him in there many times over the past year and we acknowledge each other, smile etc. unfortunately I’m too shy to ask him face to face if he would be interested in meeting for coffee or having a beer. I have found him on an online car forum and I’m not sure whether I should try sending an email through the online forum or whether that would that be stalkery and rather creepy? Any thoughts?

Thanks,
T.

P.S. I’m in my mid 40’s and he’s a similar age.

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Hi there,

I was with a guy for just under two years and in that time, I included him in my busy social group. I have a very large, very close group of friends that I have been friends with for nearly a decade. When I met my ex, he didn’t really have any friends of his own but made a few friends in my group and was friendly with just about everyone. We broke up 3 months ago due to him having kids and me not wanting kids, which I have a lot of guilt about, despite knowing it was the right decision for both of us.

Here’s the problem. He’s still showing up to our parties and events. I KNOW I can’t tell him who to be friends with – but I also wish he would stop coming around. I already have one ex in the group, my ex-husband, which is awkward enough, but we made friends with these people at the same time. This guy was only around for maybe a year and a half and while my friends liked him well enough, he was definitely still seen as MY boyfriend and not a member in his own right. Cliquish? Yeah, probably, although no one would ever be unwelcoming to him and as a group we are HEAVILY infested with Geek Social Fallacy #1 so I doubt that he’ll stop being invited to things.

I feel like a giant, selfish jerkwad because I know he doesn’t have (m)any friends of his own so he wants to cling to the ones he made through me and he IS a good guy – but I also feel like these are MY friends and having him around is uncomfortable and awkward. It will be even more so as I have started dating someone else and while I’m not ready to start bringing the new guy around yet, I will at some point and then will have to deal with him meeting not one, but TWO of my exes.

I don’t know what to do about this as I am fully aware of how selfish this desire is and that I sound like a total jerk. I know that a lot of this is a reflection of the guilt I feel over our break up and seeing him just reminds me of that, which I understand is my problem and not his. I get that I can’t tell him not to come around anymore, but short of just stopping going to events myself, what can I do? Do I just have to deal with this or is there some middle ground I’m not seeing? If it is something that I just have to put on my big girl panties and deal with, do you have any suggestions on doing so?

- Not normally a jerk, I promise!

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Once a month I try to answer the things that people typed into search engines to find my blog as if they are questions. It’s an exercise in mixed results.

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An antique brooch with a woman being bored by a man in art history (a la The Toast)

“Eugene, dear, why don’t you run and get your lute? Definitely go away. I mean go and get it. Your lute.”

Hello there, Captain Awkward,

I’m a young person and I recently ended my first relationship. We did truly love each other–even though I’m young, I can say that with absolute conviction. But there were many serious problems in the relationship: they had a horrible, rude friend who would flirt with them constantly (one time she actually kissed them on the cheek while in front of me) and despite my begging they refused to do anything about her. They were into Nazism, which I know sounds bad but they were more into the German Nationalism and never hated anyone, so I convinced myself it was “okay” even when it gave me the heebie-jeebies. However, that wasn’t even the biggest problem in our relationship, which was that they never seemed to care. They would say that they loved me, which I’m sure was true, and yet while I was fighting constantly with my semi-abusive father about them (who yells and feelings-shames me), they refused to even tell their family about me. They would go on and on about their interests and never asked about mine. We went on two dates during the whole two years that we dated, and I had to initiate both of them. They never had time to talk to me and they never could just spend time alone with me, despite how willing I always was to make time for them.

Yet, looking back, I can’t help but think that I didn’t do as much as I could have. Sometimes, they were just worth it. Sometimes they would be sweet and I could really understand why I fell for them. They certainly wouldn’t mind taking me back; they told me that they would always love me and in the week it’s been over they’ve been radiating Cher Lloyd vibes. And I don’t think I could ever really find anyone else who loved me and understood me like they did, since I’m very geeky and I have hobbies many people would consider weird. They were really the only person that I can ever imagine tolerating every part of me, and I don’t know what to do now that I broke it off. Not to mention every person that I’ve been going to about this has been hinting to me that maybe I made a mistake, which I can’t help but start to wonder as well.
What should I do? Did I make a mistake?

Sincerely,
Am I walking away from Sephiroth or Cloud?

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The Emperor from Star Wars saying "Be My Pal-Patine." There’s an Awkward Meet & Geek this Thursday at Geek Bar Beta in Chicago. Games! New people!

This guy who wrote into Carolyn Hax sounds FUN and definitely does not remind me at all of someone reading a consumer report trying to find the best smartphone. “What if I find something with great battery life and an intuitive interface, but the color I want is not available?” :flashes Bad Advisor signal in the sky:

And now a question:

Hi Captain!

Any thoughts about surviving St. Valentine’s for a single-and-never-ever-been-on-a-date-much-less-had-a-SO student?

Many thanks! And thank you for the whole site.

all the best,
OortCloud

Hi Oort Cloud!

Use the day to:

  • Han Solo: "I'll be celebrating Valentine's Day Han's style...Solo." Do something nice for yourself.
  • Do something nice for a friend or family member. There are lots of kinds of love, and there are lots of people in your life who might like pancakes or a new book or a card or a mix tape.
  • If you’re feeling down, ask your friends to be nice to you. “I’m feeling a bit blue about Valentine’s Day. Anyone feel like having Palentine’s Day?
  • Do something nice for a stranger – paying for the coffee of the person behind you in line, volunteering somewhere, shoveling sidewalks in your neighborhood.
  • Do you have a crush on someone? Perform this outside their window.*

It’s a perfectly good Saturday, so:

  • Don’t beat yourself up for not following a certain script in your life. If you read the site, you know that the “haven’t had a date or a significant other yet” club is large and adorable.
  • Don’t buy the necklace made from 2 butts stuck together.

Sometimes it feels better to make cutting remarks about how it’s a stupid made-up holiday created by advertising executives and greeting card companies and nurse your fierce proud cynic’s heart. Do what you feel, but try to do it without pooping directly on someone else’s fun, ok?

 

*This is a joke. Do not play this, or any music, outside someone’s window.

Hi Captain,

I am a single man who, after the end of my last relationship, took a
few years out of the dating scene to really rethink what I want out of
my love life and learn to be happy with myself. (For context, I’m 32,
my divorce was 5 years ago.) I feel ready to come back onto the
market, but I’m finding it hard to meet single women who actually
inspire my interest. I’ve tried online dating and singles events, but
they don’t really work for me.

Far from sitting idle, I have become more and more active in the past
couple of years about pursuing my hobbies and interests, which has
helped me extensively expand my social circle. However, it seems that
every time the circle grows, the women I meet are either happily
attached, gay, or just folk I’d rather have as platonic friends than
romantic partners. I’m thrilled to make all these great new friends,
of course, but there’s more I want out of life than my platonic
friends can give me.

Cutting back on my hobbies and going to more singles events would be a
false economy; I’m at least making new friends through hobby events,
whereas singles events have given me nothing. At the same time, I
don’t have time to cram in even more regular social activities – not
without ending up with such a busy schedule of commitments and
responsibilities that there isn’t actually space for a relationship in
my life anyway.

This being the case, I’m thinking about outsourcing the problem by
asking trusted friends to try and introduce me to single friends of
theirs. Since I’ve put in the work to expand my social world in the
first place, why not enjoy the benefits of that expansion? Plus I’d be
more confident making contact with someone a friend has recommended
than a total stranger.

That said, how do I:
- broach the subject in a way which makes it clear that this is a
serious request I am making of my friends without sounding needy and
pathetic?
- make it clear that if people don’t want to play Cupid for me we’re still cool?
- make the point that I’m not up for “blind dates”? (I’d like to know
a bit about the person in question before meeting them so I can
politely decline suggested matches which clearly aren’t going to
work.)

Yours,

The Last Turkey In the Shop, UK

Dear Turkey:

I have thoughts! on your question.

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