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Captain Awkward’s Dating Guide for Geeks

Hello,

I am a 22 year old male and my crush is a 19 year old. We met by chance a few months back.
The first time we had a proper conversation she said that she didn’t want a boyfriend.
So, I eased on the flirting completely. After a couple of meet ups I started receiving signals from her. It may have been my wishful thinking.
I take her out for a movie, one thing led to another and we kissed.
When I dropped her home that night, she said she doesn’t feel the same way. So, I let it go.
The following day I receive a text saying that she didn’t want us to continue being friends anymore because she feels awkward and she can’t deal with it.
I have strong feelings for her. More than anything I don’t want to lose her.
Kindly Help!

Thank-you.

Hello Yourself!

I guess you are part of a recurring theme, writing in the day after this posted.

This woman doesn’t want to be with you, romantically, or as a friend. She told you this directly. She, not I, not the Internet, and definitely not you, is the sole authority on this question, and she has communicated her decision quite clearly. The only right decision here is to respect her words and leave her alone. If at some point she misses your friendship, she knows how to find you.

Sometimes people don’t make up their mind about you all at once. They need more information, so they do things like “go on a date with you and kiss you” to try out the notion of you. That’s what happened here – she gave your kind offer some more consideration – and then she made a decision. You can’t “lose” her because “having” isn’t a thing; there is only choosing, and being chosen in return, and not being chosen.

I have had people try to convince me that I was wrong to break up with them or to decline to deepen or continue a relationship. The trajectory of those interactions ranged from sad to annoying to terrifying. I have tried to convince people not to break up with me, to give me one more chance. I can only pray that they (plural ‘they’, unfortunately, not the groovy gender-neutral singular construction) have long since deleted the Emails of Desperation and Neediness I sent. You’ve all seen how wordy I can be here, now imagine that “talent” and energy applied to convincing you that you really, really should stay with me even though you don’t want to, complete with numbered lists of reasons and airtight logic cases for why it really, really should work out.

Picard, Whorf, and Riker with Facepalm

Hounding those people – people who genuinely liked and cared for me but who just didn’t want what I wanted – is one of my true regrets in life. I would give a lot to be able to take it all back, to disengage more gracefully from those past relationships, to save my dignity, their patience, and to be true to a principle of consent in all things. Fortunately, I did eventually learn that you cannot logic someone into loving you back. My life got so much better when I learned that lesson and I hope yours does, too.

I know it’s terrible to contemplate losing both your hoped-for romantic connection and a friend, and I sympathize greatly with what you must be feeling. Please, take the time away from her as the gift that it is. Delete her number from your phone, hide/unsubscribe/unfriend her social media feeds, lick your wounds, grieve for what might have been, and throw yourself wholeheartedly into other connections and interests. Read books by women. Let time do its healing work (It will, I promise). Be a person who takes “no” for an answer.

Dear Captain Awkward:

I am 13, and the girl I love is 16. I have a higher IQ than I should at this age, so believe me I am 13. Anyways, I have been talking to this girl for almost 3 years. Throughout this she has had the same boyfriend, R. About 2 months ago she broke up with R, so I was kind of uneasy. I really wanted to expose how I felt to her, and I have flirted with her before, which she said I was cute. So anyways, I pretty much just vented my feelings to her and I think I might have caught her off guard. She declined my request to be her boyfriend even though as of now we have been best friends for 2 of the 3 years. She said she had a lot on her plate because she was moving from Texas to Tennessee. I live in Ohio, so this is sort of long distance. What do I do to show her I truly care for her?

Dear Letter Writer:

To show your friend that you truly care for her, believe her. 

Believe her when she says that she doesn’t want you to be her boyfriend.

Believe her when she says that she has “too much on her plate.” The translation for “I don’t want to/can’t be in a relationship right now” is “I don’t want that kind of relationship…with you.”

You were brave and honest when you told her how you felt. You didn’t do anything wrong when you did that, in fact, you did something wonderful and cool. But now that she’s told you that she doesn’t feel that way, it’s not up to you to make any more grand gestures to try to change her mind. If you need to take a break from talking with her or even stop being friends for a while because it’s too hard, that’s okay – limp off the field, lick your wounds and take all the time you need. Channel your feelings into writing songs or poems  or stories (that you don’t send to her) or finding another creative outlet and throwing yourself into it. Friendships can survive unrequited crushes, but they really do fall apart when one person won’t take no for an answer. You can’t win her heart right now, but you can respect her choices and show her that you do by giving her time and space.

Dear Captain Awkward,

I’m newly single, and getting back into dating. I went on a date last night with a guy I met on OKC. We met up at a bar, and he seemed cute and smart, and as we talked it seemed like we had lots in common! But about twenty minutes in, it seemed clear he wanted to do the touching-kissing thing. I had just met this person, and I wanted to get comfortable around him before I let him put his hands on my body (even though he was cute and promising!). So I was sitting kinda sideways and he was sitting facing me, legs apart, physically accessible, etc.

He said something like, “You’re very guarded. I’m in the restaurant business and we read people quickly and I can tell that you’re very guarded.”

I felt weird, but there was this voice in my head saying, “You never let yourself just flirt and have fun!” So I sat facing him and let him touch my leg, and we kissed and had drinks, and the conversation was good! And we had a lot in common! And he was a good kisser!

Then he told me about a male friend of his in the military who got falsely accused of rape. Apparently the guy was going down on the woman, and she told him to stop, and he didn’t. She made a rape accusation and then later said she was lying.

So this guy (my date) said, my friend didn’t penetrate her—it was just oral sex! She didn’t physically resist! She made that accusation about three other people! She said she was lying!

I was thinking, 1. That was rape. 2. Wouldn’t be surprised if three other guys also didn’t listen when she said to stop, because that isn’t uncommon. 3. Women retract these accusations under pressure all the time. Warning lights are going off in my head. But I didn’t want to get into a fight about rape with a stranger. So I redirected the conversation.

Then after a while he said “I would really like to kiss you in a place other than here.” I took this as “I am ready for you to invite me to your place now.” I was caught off guard. So I said, “I don’t think I’m ready to sleep with you yet.”

So he said saying, 1. I just want to make out! I never said anything about having sex! 2. We should do this soon because the attraction is here now and if we wait it will fizzle out. 3. Are you worried about being a slut? I feel pressured and uncomfortable. He asks what’s wrong. I say, 1. You told me about how you think things that are rape are not rape. 2. Now you are pressuring me to take you home with me.

He was immediately horrified. He started saying “Calm down! Relax! You shouldn’t be so anxious!” I felt more and more uncomfortable. Finally we parted ways. I went home and sobbed. I have no idea why. I think I missed how easy it was between me and my ex, and now it’s like, ahhh, weird dating is my new reality!! Plus I just felt sooo uncomfortable.

My questions are, 1. Is it weird that I really don’t like being touched or kissed within 20 minutes of meeting someone? I Is that what’s expected these days? It happens to me a lot. I think everyone is reading Neil Strauss and think they have to “kino escalate” immediately.

2. Is there a script I can use when someone tries to touch me before I’m ready? One that is friendly?

3. I’m looking for my next meaningful relationship, ideally, but I wouldn’t be against having a fling. But I feel my idea of “casual sex” and most guys’ is different. Mine = we go out! We flirt! We go to art galleries and museums! We have sex sometimes, once we’re ready! But not very often / we date other people. Theirs = I expect sex immediately when we meet, and thereafter whenever I text you even if it’s 2AM, I expect you to come over and service my needs.

Does anyone have experience expressing what their idea of casual sex is and guiding the other person’s expectations toward that, provided casual sex is something they want too? I feel like what happens is I run into this “We must have sex right now!!” expectation and then I flee.

And finally, 5. Should I have calmed down? Was I overreacting about this guy’s creepy rape story? Intellectually I don’t think so, but there is a loud voice in my head saying “You ruin everything by overreacting all the time!!”

Thanks for your thoughts!

Awkward Dater

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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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