There is this former co-worker Tara I've liked since I met her years ago. The timing was never great though. For the longest time she was a supervisor, and I was not, (though we are close in age). Then I became a supervisor too and being peers we worked together more and our casual in office jokes etc... became more frequent and we would text, be on Facebook, hang out on break together, but she was off and on in a relationship. Then she got engaged. I was just about to seriously ask her out because I was leaving anyway. Last December I was at my current job about 3 months in. I saw that she was single and I asked if she wanted to catch up and do lunch. We did and had a great time though I saw the breakup was still fresh. Tragically, he died a few weeks later. It obviously was still very hard on her.
This summer I entered a relationship but that is pretty much over now. We have slowed things down and are open to seeing others, despite still liking each other and spending time together. I hadn't seen Tara in person since spring of this year, but we had occasionally sent some jokes on FB, or commented on football. I actually avoided to much contact with her for fear of emotional cheating. Well I texted her this past weekend and said I was planning on doing some Christmas shopping in the mall where we worked together (she's still there). I asked if she would want to have lunch together. We made plans for the next day.
It was great to see her again and enjoy her silly/sarcastic humor. We both talked about how hard work was lately and what was new with everything. Simple stuff. That night she sent me a couple funny memes on Facebook. Nothing related to anything in our conversations; just random. Those prompted more joking back and forth. It was fun. She hadn't posted anything to my wall in nearly 8 months.
I know she's a big Disney fan so I waited 2 days then texted if she wanted to go see 'Frozen' with me sometime this weekend. She told me she was super busy with work (which she truly is. 6 days a week nearly), and she had plans with a mutual friend on her day off. I told her have fun but we should do something again soon because lunch was fun. She said 'Definitely we should. It was fun!'
Now maybe she just wants to be friends. IDK. I want to get in a position where I can truly ask her out after not having the chance for four years.
What is now a good way/time to do that? Call her? Text her? Ask her out on a date, or just as friends and wait till in person (this is my preferred)?
Most Helpful Girl
I would say just give her a call some day after dinner. Let her know that you miss her and would like to hang out, but also let her know that if she's uncomfortable with it or would like to not that's fine, too. At some point you're going to have to discuss your feelings about her, with her. So find some time to hang out and be able to sit down and do that. But approach it in a non-threatening way. "Hey I know that we're just starting to hang out again but I think I have some feelings for you and I guess I just wanted to let you know how I feel and was wondering if you'd be open to going on a date some time. Not as boyfriend and girlfriend, just as two friends seeing if they could be more." DOn't say that over the phone, do that in person, but do call sometime convenient for her (and you) and talk about how she's doing, if she wants to hang out sometime.1