Today on Ask Dr. NerdLove, we’re going to do things a little differently. This particular writer wrote a long and detailed report, wanting to know what he could have done better. So instead of just the usual ask-and-answer routine, I’m going to break down exactly what he did right… and what he did critically wrong.
I will warn you now: I am not terribly merciful when it comes to these. Over the years, I have learned – through brutal personal experience – that a soft touch doesn’t always work well when correcting mistakes in one’s game. So with that in mind, brace yourself folks, it’s gonna be a rough one.
I am trying to go out with a girl from school. I met her a few trimesters ago while passing by a teachers class and complimented her on her drawing technique.
A lot of people will tell you that asking a girl with a sketchbook what she’s drawing is a bad way to start off hitting on a girl. I disagree. I’ve almost always gotten a good reaction. Admittedly, being an artist and being able to talk about art intelligently helps here.
But I digress. This? Good way to start.
I didn’t see her for about a month later (medical reasons)
Um… right. Ok then.
After that she stops me in the hall way and we proceed to flirt and talk about stuff for like two hours.
(she was going to a class but decided not to go so she could stay and talk to me)
This is what we in the biz call “A really good sign”. She couldn’t have given you a bigger indicator that she was interested in you if she used semaphore flags.
A couple of days later she comes looking for me and we talk a little more. After a couple of minutes i tell her she has to leave cause my boss was giving me the stink eye.
Telling her she had to leave because she was going to get you in trouble… great flirting line and an excellent example of a fake time constraint. Except you weren’t flirting here were you? I’m guessing that you were being completely serious.Even if you were, the best thing to do here is to say it with a grin and a bit of a tease in your voice, just to make sure you don’t sound as though you were saying “Get lost kid, ya bother me.”
Also, I notice that you don’t get her number. Once again, she is doing everything short of beating you over the head and asking you out.
Then about one or two weeks later she finds me on my way to lunch and invites me to eat with her.
I stand corrected. Looks like she got tired of you waiting to take the hint and took the initiative herself.
Pro Tip: WOMEN WILL ALMOST NEVER DO THIS. DO NOT WAIT FOR HER TO MAKE THE FIRST MOVE.
(I tell her, I dont have a car cause its broken.) She takes us to lunch. The first place we go to has no ATM so i tell her I don’t have any cash on me. She offers to pay….I told her that if she paid, that this would officially be a date. She then chuckles a little and suggests some other place. We go to that place and we proceed to talk shit and flirt for about an hour or so.
And this is the part where I start pounding my head into my desk. For fuck’s sake, she has done just about everything other than crawl into your lap and start to wiggle. Teasing her about this being a date would be good… except for what’s happened afterwards where you seem determined to snatch defeat from the jaws of victory.
She then for some reason talks about shoe size…..I proceed to try to tell a joke about how foot size equals to the size of how big your shoe is (fresh prince)…
Not the way I would have taken it, but a joke is a joke and there’s something to be said for taking it in a different direction and teasing her for having a dirty mind.
…and just as i was gonna say it she starts talking about how her sister told her about a boyfriend who had big feet but a small penis and that her ex-boyfriend had regular sized feet and a regular sized penis……
Immediately cut her off and tell her “You know I’m not gay Right?” “We are having a conversation about penises”
OK. I’m going to try very hard not to vent my frustration here. The topic has turned to sex. This is a good thing. She is signaling to you that she would be interested in talking about your penis. There are many ways that you could have taken this conversation. You could tease her about being a size queen. You could say “Clearly we’re never going to get along. I’ll totally never measure up to whatever weird fantasies you have about me and you’ll be telling your friends how you couldn’t date a guy who was only above average.” You could tell her you’ve got a micro-penis but that’s ok because you can lick your own eyebrows. Instead you killed the entire topic by making a really ill-advised gay joke.
And if you were really concerned that she would think you were gay because you were talking about penises… Dude, it’s the 21st century, get over it.
Pro Tip: If a woman starts taking the conversation in a sexual direction… you let her.
She looks strangely perplexed …
I’m not goddamn surprised. She should be perplexed! Not only are you apparently getting weirded out by a conversation topic you started, but you’re shutting down her attempt to lead things to sex!
…and then I suggest going to the movies. She call her mother to tell her about her plans. (she lives about two hours away and she has an apartment while at school, the day we went out was the day she was going back to her house for the week.)
Well at least she’s still invested in this date. You still have a chance to pull out of your death-spiral here.
I immediately tell her I am not gonna see “Something Borrowed”
Pro Tip: When a girl is being nice to you, you want to encourage this behavior by being nice back. Instead of, say, being an ass-hat.
She tells me its Ok cause she promised to see the movie with her sister. We chose another movie but the time it was showing was about an hour away. So i suggested taking a walk around the plaza. We proceeded to walk, flirt and talk shit for another two hours.
Once more with feeling: Life has handed you this on a golden platter if you weren’t insisting on doing everything in your power to screw things up.
She then left me at my house and asked for my phone number just in case she got lost on the way from my house to where she was going…….
Apparently she’s gotten tired of waiting for you to get her number.
I didn’t hear from her until like a month later…
BECAUSE YOU DIDN’T CALL HER.
She was working at a place for the summer and she said she wanted to have lunch with me. (the place she works is easily 30 min or more from my house) She then wanted to sneak me in her building and keep me there for a couple of hours. I proceeded to humor her for an hour or so and then told her I had to leave and that she should go back to work.
Aaaaand? Did anything happen or were you just there to hang out? Going by the fact that you were “humoring” her, it seems as though nothing did. Despite her best efforts.
After that I only called her once three days later to see how she was……(no word back)
OK, if there’s any stupid “player” advice I wish I could make disappear it’s that damn “don’t seem too eager, so wait to call her” rule. Actually, no, I tell a lie; I’d start with the goddamn “negs” and “cocky-funny” business since nobody seems to understand them but that three days rule is a close second. In any case, I’m not surprised you didn’t hear back from her. I am astounded, however at this next part.
Suddenly a week ago i saw her walking towards me just after i left work. She was hanging with her sister and two other friends…..she said she was happy to find someone she can have an intelligent conversation with and that she’s tired of listening to her sister and friends talk shit.
I joked and told her that i noticed that, and that she practically ran towards me. She hit me in the shoulder and told me she wasn’t ….I then told her Ok she skipped towards me. She laughed and we started talking. (after a while i decided in my head i would ask her out again, but then she started talking about how she was hanging out all day with her sister and friends.)
Right here? The part about teasing her about how she ran towards you, then following it up with skipping instead? This was a good move. That’s an excellent example of both teasing her and setting a frame that she is pursuing you. I am goddamn astounded. Congratulations…
I don’t remember if i told her i had to go or that her sister called her?
… except you missed another golden opportunity to ask her out. Even if she wasn’t able or willing to drop everything to go hang out with you right then, you could have easily made plans for later.
(my friends said i should have asked her out anyway even if she was with her sister and friends, that if she liked me she would have omitted there presence and hanged with me even if they where there and that if she said no i would have an idea of what she thinks about me)
Your friends were right. You should have asked her out anyway.
Sorry for the long convoluted story just wanted a fresh opinion and i didn’t want to leave anything important out of the story.
So going by the way things end, I’m working under the assumption that you still haven’t asked her out. If she’s still interested in you, I’d be downright amazed since you seem to be doing everything in your power to make sure she loses all interest in you.
At this point, if she is still interested in going out, I strongly suggest you dial your tendency to be aggro and pushy way the hell back and go with the flow. If the subject matter turns sexual, you’re in a position to escalate things… provided you’re willing and able to see the signals she’s sending you and respond to them. When a woman you like is giving every signal that she’s into you, you get out of your own damn way and run with it.
Otherwise you’re just making things harder for the rest of us.
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