I went out of my comfort zone. Where was my mistake?

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super shy guy 88 asks:
Went to a bar after work, a girl there kept giving me eye contact. My friend ended up getting her and her friend to play darts with us. We didn’t talk a lot, just minor conversation and flirting (I’m extremely shy) but overall things seem okay. Last call comes and I can’t find my phone, so I ask my friend if he can call it, then she spoke up quite abruptly saying “I will” so I give her my number. We find it, we then go out and munch on some food. We realize its 2:30 am so we hug and say our goodbyes. I get home and I figure, screw it, I’ll go for it. I text her around 3:30 am asking “Is this Jane from the bar that helped me find my phone?”. She said yes and she thanked me for the food I shared with her. I said no problem, thanks for helping me find my phone. I then asked her if I could take her out to dinner or something sometime to repay her for the kind favor. I haven’t heard back little over an hour later.

Did I come off too strong? I’m very bad at this :\

Demetrius says:

Buddy, what makes you think you did anything wrong? Seriously man you’re asking this question hours after you met. It might be too early to tell whether or not she’s actually into you or just really eager to help people, but if I had to guess I’d say she’s into you. You didn’t make any mistakes, and honestly you did a great job of showing interest despite how shy you are. Normally I take these questions, dissect them, then show you were you went wrong, but today I’m doing things a little bit differently. Let’s talk about what you did right, and where you could improve. We’ll start with the areas where you can improve.

The night would not have happened if not for your friend being the one to get those ladies over to you so in the future, if you’re getting clear signs, don’t be afraid to make a move. Best case scenario, you get an amazing night out of it, worst case scenario you get a “No” and still get to drink with your friend. That’s a win-win situation in my opinion. Once someone engages with you and your group in an active way, feel free to talk to them. The people who don’t want to talk to you will make it clear based on their body language and disinterest. The people who will want to talk to you will stick around, engage with you and your friends, things like that. If she was doing all those things, talking to her wouldn’t have ruined the night, so try to engage when people seem to want to engage. Again, it’s another win-win scenario. If you chat her up and you hit it off, a win. If you chat her up and she’s disinterested, you know that you gave it a shot which is a win in and of itself.

With that out-of-the-way, let’s talk about where you did really well. For starters, taking her out to get post-drink food was a great way to turn a chance meeting at a bar into what was essentially a half-date. You’ve already setup a comfort level that you can build on when you see each other again and that is invaluable. My go to move when I meet someone who I hit it off with at the bar is to get some post bar drinks if the bar is closing. If you can pull that off, chances are good that she wants to see you again, or that she needs a good sober food. The follow-up text was also a strong move. Even if it was brief, you signaled to her that you not only remember her, but also that you were thinking of her. The continuation of that, the follow-up text asking her out again, was also a strong move. I know you might have some doubts about it but trust me, it was the right thing to do. I wouldn’t necessarily have sent that text at 3am but the context in which you sent it was appropriate. You knew she was up a bit ago so it wasn’t like a booty-call type text, it was a continuation of a conversation.

Honestly, you might be shy but you’re better at the whole dating thing then you might think. All you have to do is fight the instinct to not speak and you’ll get better at it. I’m 75% certain she’ll get back to you after she gets 8 hours or so of sleep so don’t worry. If she doesn’t, don’t think of the night as a waste or a failure, think of it as practice for meeting the next person. If you get comfortable talking to people, you’ll find that no matter how shy you are dating becomes a lot easier.

Good Luck Out There.


5 thoughts on “I went out of my comfort zone. Where was my mistake?

  1. Agreed, D! A lot of people might think the 3 am date text should’ve waited, but if you’re into someone that’s not going to be a turn-off. If she’s into him, she’ll be excited that he asked her out again so quickly. But the fact that she didn’t write back for a while (if at all) is probably a good sign that she’s not into him (unless she passed out!)

    Liked by 1 person

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