How can I reveal my true feelings to a long-time coworker? We work great together, but recently I've discovered that I'm interested in dating her.?

First, some background information. I have worked for my company for nearly 3 years and have been in management for the past year and a half, but have worked with a particular manager the entire time through two different locations. At first, we didn't really get along, but that began to change after my promotion. She took me under her wing while I learned the job and we have worked well together ever since. The last few months, I feel like we have been super comfortable together, particularly when we are the only two managers around. She has been hanging around after her shift just to talk to me, and the conversations have been getting progressively personal and even a bit flirty at times. This is very unlike her as this woman is pretty well known for how quiet and to task she is. I've never been one to look at a coworker romantically, but have been unable to drown those feelings here. I feel like she has left some signs that she likes me, such as her increased eye contact and being almost overprotective of me when something goes wrong during the shift. And she has this huge smile that I'd NEVER seen from her until recently that I get during our more personal conversations.

She is going to be transferred out in the next few weeks, so it appears unlikely that we will work together again for a long time, if ever. But we only live 2 miles apart so distance wouldn't be an issue. What are some good ways to tell her that I am interested in getting to know her outside of work? She is a bit older than me (31 to 26) and has been single for as long as I have known her, so I think she would be pretty cautious.

  • Tell her how I feel BEFORE she transfers
    Vote A
  • Contact her shortly AFTER transferring and she has had time to get settled
    Vote B
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Most Helpful Girl

  • Don't even directly ask her on a date, just invite her for coffee or something simple, like a friend thing. That way once you two get away from work you can kind of feel out if she likes you because she will let her guard down.

    • Thanks for the advice! She is transferring later this week. I asked if she'd want to catch a baseball game a little bit down the road and told her that I want to stay in touch. She said yes to both and seemed pretty comfortable with it. Somehow I think she knows I'm interested in her as something more than friends just from the way she's been smiling at me lately, but I don't want to come on too strong too early and scare her. So my goal is to keep in touch (texting, maybe a phone call), hopefully meet up outside of work, and then let things evolve if a connection is there.

    • Awesome! Good luck!

    • This is a great answer.

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What Guys Said 1

  • I'd wait until she leaves. Far less chance of drama/her telling everyone that you asked her out.