How to Stop Getting Hung Up and Overthinking A Specific Girl?

I'm still a bit new to the dating game, but overall I would say I am very cool with being rejected. I don't take it personally and the last 4 girls I've asked out have either turned me down or turned down a second date, but we're still at least casual friends. Two of them are very good friends that I care about, see weekly, and are very healthy relationships, not one sided at all. I don't overthink the rejection and I'm very relaxed and confident both when I was asking and after I was rejected.

However there is one girl I know and am interested in that I just can't get myself to stop overthinking things with. I don't know why, but I am extremely nervous around her. I've known her for ~2 months and I think I've managed to maintain a confident attitude and make a good impression with her. We've not had any deep conversations, but we had a few slightly flirty and friendly interactions with some good laughs.

We also work at the same company, but I only moved to the same location she worked just this week. I told her last week that she and I should grab lunch together sometime, and she said yes, but I found out she works 3rd shift so our shifts don't overlap at all.

I guess the biggest hang up is that she recently was excited about finally going on a date with a guy she'd known since middle school. That was a month ago, and I haven't heard anything since, but she could just want the privacy.

Any advice on how to stop putting so much pressure on myself with this one particular girl? What's the best way to go about finding out if she's still going out on dates with this guy?

If I knew she was single I was thinking about joking asking her out by asking if she has a limit on how tall of a guy she'd be willing to go on a date with, since she is just under 5' tall. I've joked about her height before with her, so she wouldn't be offended at all. I just don't want to ruin my chances by asking when she isn't single.

Anyone have any advice?


Most Helpful Guy

  • Good man, she accepted to do lunch with you, so following through with her by attempting to set a date and time, I believe, should be your next course of action.

    Who? The other guy? What other guy?

    By all means, do not ask her about or make reference to another guy she has gone on dates with. What she did and does with him should be no concern of yours. As far as you know, she is single, mingling and dating. So, do not let her dates with this guy, or any guy, discourage you from pursuing her. That is, unless she personally and specifically states otherwise.

    To answer your question; your fear of losing her to this guy has caused you to repeatedly overthink things. It's insecurity at work. Thus, I simply suggest that you ask her to lunch upon the next time you interact with her. A lunch during which you ask her out on a date. If, of course, you are confident to handle any outcome.

    By the way, whether she is single or taken, asking her will not ruin your chances, in the least. . However, not asking, will almost certainly decrease or eliminate your chances with her.

    • What a really great response! I like his advice, I also agree he should follow up with a lunch, and NEVER ask her about her other dates, just stay flirty. the minute he asks about the other guy, she will start treating him more like a friend disclosing details she would to a friend not someone she'd date.

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  • I agree with the staff seargent and I think you shouldn't get hung up on her yet. In fact you should keep your options open even if she is the main girl you want. Still try and talk to other girls you're attracted to just in case she doesn't turn out to be the one for you.

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