Trying to date a coworker

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Trying to date a coworker

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  • Hayley Matthews Hayley Matthews
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    Anonymous
    October 30, 2015 at 11:28 am #87679
    Trying to date a coworker

    Recently started hanging out with a coworker and became friends. Been going well, I’ve developed feelings for her (not just a “crush”). We’ve had numerous deep talks, even til 5AM in the morning. But she’s social and has done that with other friends.

    THE ISSUE:
    She’s a mom (that’s fine), 2 jobs, busy schedule. She has had boyfriends through this but not good ones. Trust me, I know I’d be better. Consequently, she seems hurt, careful with dating, said her next guy will have to wait 1yr for sex (and I don’t believe in one-sided rules).

    No idea if she likes me or not. Did tell me I’m smarter, more of a man than her ex’s (but that doesn’t take much).

    What’s the approach here? Flat out ask her out or wait?


    Raveboi
    Participant
    October 31, 2015 at 12:25 pm #87730

    Yeah! Ask her out, sounds like your golden.


    Whitney
    Participant
    October 31, 2015 at 1:59 pm #87733

    Yes, you should ask her out. Take it slow, show her that you genuinely care for her. Good luck!


    Anonymous
    November 1, 2015 at 10:40 pm #87742

    Thanks!


    Anonymous
    November 13, 2015 at 8:51 am #88393

    ******UPDATE*******
    I’m in a really tough place. I decided not to ask her out after she’s been adamant about staying single for awhile. Which I do actually understand why. But I feel strongly for her (I haven’t told her) and not sure what to do. Just move on or wait to see if a friendship blossoms? Normally, I’d call it quits but this one is different.


    thatguy218
    Participant
    November 15, 2015 at 6:22 pm #88496

    You should show her why you’re better than the “last,” and be patient with her. Sounds like she’s had some bad experiences in the past and needs someone like you.


    thatguy218
    Participant
    November 15, 2015 at 6:23 pm #88497

    Also make sure she knows you’re still interested.


    JD123
    Participant
    November 16, 2015 at 8:41 am #88458

    tread carefully because the whole ‘don’t eat where you sh*t’ things comes in with co-workers. at the end of the day if you feel greatly for her you need to be honest and let her know where you stand. don’t be blunt and cattch her off guard though. see if you can get her out for a nice meal or something. if things go really well you need to say to her that you really like her and would like to know where she stands with things. 99% or girls love attention, compliments and being wanted. worst that could happen is she says she’s not in that place right now, hopefully you haven’t ruined the whole work environment, you’ll get over it soon enough. if she likes you then top notch


    Anonymous
    November 18, 2015 at 6:02 pm #88707

    Thanks for the replies. The fact is this isn’t great timing. I know 100% nothing will happen for awhile (if at all) so I can’t say anything yet. My approach is to keep being her friend, “kill her with kindness,” and revaluate things in the future. Go with my “gut.” Good approach?

    Then again, waiting around seems to NEVER work out…ugh.


    dionusos
    Participant
    November 18, 2015 at 11:07 pm #88708
    Reply To: Trying to date a coworker

    I’m in a similar situation. When you talk to her on the phone, what kinds of things do you two discus?


    Anonymous
    November 19, 2015 at 12:11 am #88715
    Reply To: Trying to date a coworker

    We don’t talk on the phone. We both hate the phone, haha. She’s busy as all hell so we talk at work and text. Joke around a lot, shared quite a bit of private stories, occasionally hang out. Like I said, we’re friends.

    It’s tough cause I know if anything were going to happen, it’s gonna take time. That’s the only fact I know. I know her well. But then again maybe I’m waiting around for nothing is the issue…