How to follow up a date for a drink!?

I've been sweet on a woman at work. She works in a different department. I work in IT. I've known here for about a year. I helped her many times with PC issues, saved her from embarrassment once. She is the nicest kind caring woman I've ever met. Well the last job I did for her she said she owed me a drink. I said well careful I'll hold you to it... I didn't really expect anything from it ... Well I was wrong. Out of the blue she calls me and asks me about that drink. Of course I said yeah! We haven't picked a time or place yet... She has adopted kids and is busy... And I'm trying not to over play it.

Her last day at work is Friday, wants help with one more PC issue, but still wants a drink with me.

So, what do you think. I'm pretty happy but nervous. I don't think she is using me for work, but she might.

Should I just pick a date and a place and let her know? And how do I follow up to get another date!?

I really like this woman, and I'm not intimidated that she has kids I want this to work.

Updates:
I think sh likes me. Invited to her office, small talk, made some sort of plans on where to meet. She talked a little about her kids and finances and time she has, I said okay no problems. She always smiled, her outfit showed off her legs & she flaunted without care of me looking.


She didn't get any going away gift or card or even a goodbye. I gave her a Russell Stover 4piece chocolate. She gave me a big hug and sunk her head deep into the side of my own.


I think I nailed it
So, flowers? Also I know people say kahkies but all I have is black dress slacks, I do own nice jeans that are dark blue. What to wear... Also kiss on first date?
She could not make it today, but she called immediately to make sure I understood why. She really has no one to help her with the children since the babysitter has a torn ACL. She wants to get me out on Sunday. She has a slot where she had the kids being watched for a BabyShower.. She's thinking of ditching that early to go with me instead.


I'm not holding back like some of your answers seem to think I am. On the contrary, I'm actually calling her, and I know where we're going

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Most Helpful Girl

  • Just pick a place and time and tell her. Is she leaving the company? you said her last day is Friday. during the date compliment her about how you find her to be the nicest kind caring person you've ever met. Don't forget to ask about her kids. women with kids love talking about their kids so show some genuine interest so she know you're good with that because obviously they're the most important thing to her with or without a man in her life. At the end of that date, tell her you enjoyed yourself and would like to go out with her again. See what she say. If its a yes, you're on a roll and can take it further from there.

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What Girls Said 7

  • You are laboring on this way too much.

    Just be assertive already

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  • Get her number and get her out already. She's already made the initiative. If she really didn't want to follow through she would have never said anything after the first time.

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  • I am not sure about the flowers but maybe a modest bouquet if you insist. The first date should be casual so maybe the dark blue jeans. Not sure about the kiss, depends on the individuals. My opinions here of course.

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  • that is a really sweet story. I wish my work crush would step up :-(

    anyhoo...

    definitely follow up. if you have her personal number all the better. she wouldn't have

    mentioned it twice if she wasn't serious. she probably digs you ;-)

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  • Be yourself! Take her on a date, try and find out what she likes! This is lovely :) Good luck!

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  • just ask her, don't make it difficult.

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  • sometimes I say this to guys and I'm generally interested in them as a friend... ofcourse I never get hit on or asked out. But still just man-up and tell her that you would like to see her again or something but don't fall into a friend zone kinda thing with her. good luck!

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What Guys Said 3

  • Awesome man. That's the right attitude. Just do what you think feels right. But yes, you should be the one to pick the time and place for the date.

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    • UPDATE: Don't fail us, bro! Us single guys put our faith in you!

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    • She doesn't want to get the children into it, not at this stage or ever in her expression. She had a bad breakup with a guy that was with her and them for 7 years... I did show that I was capable of the responsibility of children by mentioning my nephews and my Niece who was from a different mother.

      I guess I'm just unsure of myself now. I'm emotionally confused, I know I can't invest my whole heart into this because now there's a good chance I can be hurt.

    • I see. So what are her intentions then, anyway? If she doesn't want her children involve (which I guess I can understand), is she then really okay to be seeking a new romantic partner? Also, don't give up hope. She's only dating the other guy, but they're not exclusive yet as far as you're saying. He may have more money and such, but mature women are able to see past that and are looking for something more real. So keep going and see what happens.

  • Dude, take the lead. She f***ing wants to go on a date with you. Ask her out.

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  • The perceptual and rational game... Get some at the same time, it will lose something simple, such as time, energy, but serious will involve work, future development.. Need to weigh the advantages and disadvantages.

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