Should I even bother going for it? (This is a really long one)

So I really like this guy that I work with, but there are a few things that make me wonder if it is even worth going through the effort to ask him out. My friends tell me that asking him to hang out is really my only option since apparently I send mixed messages because I am always really enthusiastic with every customer and it sometimes looks like flirtation.

But I’m terrified of asking him to hang out and I’m not even sure it would be worth it to put myself through the mental agony of doing so because I only work with him one day a week and we barely get to talk because there is always a ridiculous number of customers to serve, we share almost no friends in common, and two of the ones I know are guys I was sort of involved with in the past, I don’t know what we have in common (but I have made an effort. with the little time I’ve had to talk to him I have complimented him on the music he puts on at work, laughed at his jokes, asked him about his weekend, even told him whenever I thought some of the drinks he made looked perfect.), sometimes I get the sense that he thinks I’m stuck up though which is only because I get really guarded around him some days and resort to acting kind of robotic and uninterested, and lastly I have no idea what in the hell we would do or talk about if he agreed to hang out with me because I get so tongue tied around him and I don’t know what we have in common.

So, I have a few questions. Firstly, have I already screwed up my chances? Is it really important to guys that we have mutual friends/acquaintances? What else can I do to win him over? What are some casual date/hang out suggestions? Or should I just let this one go?

Updates:
Guys, please realize that I have considered the whole workplace romance thing and that I wouldn't have considered this guy if that were going to be an issue. I really just want an answer to my question.

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What Guys Said 2

  • Well its not too long and its not block-text so ill answer :)

    As far as the workplace romance thing I don't think id worry about it - especially if you just want to ask him to hang out initially? And I mean its just a part time dead end job - really no big deal.

    I don't think you've screwed up - you've still got some chances, can you talk to him at all after work or something?

    For me personally I don't care about mutual friends or acquaintances when I'm going out with a girl I like. If you ask him to hang out with you though, it might be a good idea to bring some of your friends along and tell him he is welcome to bring his. One of the girls at my workplace one night just texted me asking me to join her at her friends birthday party. I hardly had anything in common with her and was always nervous around her too - but felt comfortable knowing it wouldn't just be me and her. Other times women have asked me to hang out with them they've just told me 'me and my friends are going to this bar on Saturday - would you like to join us?'. So don't just ask him to hangout just the two of you, but maybe have something set up where he can bring some people and where you have people as well - that way your both comfortable and get to see what your really like

    I wouldn't let it go if your really interested. I mean I've let people go many many times in life and I regret it - sure there are many people out there but I think you should consider every opportunity you get. That's just my opinion though

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    • Wow, what a great help! Thanks, I'll definitely try that.

  • Never dip your pen in company ink.

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    • I have definitely thought about that, but the fact is it's a campus job and shifts are changing next semester. It's very unlikely I'll work with him again. In the 3 total semesters we've both worked there, I've only gotten one 3 hour shift with him for 1 semester.

    • Okay, well... you're in college and you will be getting a job afterward. If your interviewing employer calls your college or co-op and there was any kind of workplace romance or drama, you will not get hired. If your Facebook contains workplace drama or stupid college things.. you won't get hired. I just honestly wouldn't get involved. College is tricky, and you definitely don't want to risk it ending badly.. It will backfire, I promise. It could cost you a future career.

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