Me (27F) asking out a former colleague (34M) - how?

I (27F) worked with this guy (34M) for two years and I left around a year ago. I’ve had a crush on him for a while.

When I left work I tried to move past it, I wasn’t sure if I missed him or my whole life/job I had before and wanted a new start as was never sure if he liked me back.

I’ve seen him twice recently and I still like him. He’s friendly, playful and kinda shy, but he doesn’t single me out for conversation- he seems to actively avoid being next to me when walking down a street, won’t sit next to me on the train etc.

We went out as a group tonight as our old workplace is closing. Despite my trying I couldn’t get him alone to ask him out. I’m disappointed with myself that I didn’t ask tonight, but there was someone literally traveling with us home the whole way before we had to split off. There was always someone at the dinner table or bar. I don’t want to do it with his colleagues in earshot obviously! I don’t have his number, only work email.

There’s a final event next week. Do I (1) wait til then to ask him out, (2)or email him tomorrow? Or (3) leave it as he doesn’t seem interested?



Submitted January 21, 2020 at 11:49PM

I (27F) worked with this guy (34M) for two years and I left around a year ago. I’ve had a crush on him for a while.When I left work I tried to move past it, I wasn’t sure if I missed him or my whole life/job I had before and wanted a new start as was never sure if he liked me back.I’ve seen him twice recently and I still like him. He’s friendly, playful and kinda shy, but he doesn’t single me out for conversation- he seems to actively avoid being next to me when walking down a street, won’t sit next to me on the train etc.We went out as a group tonight as our old workplace is closing. Despite my trying I couldn’t get him alone to ask him out. I’m disappointed with myself that I didn’t ask tonight, but there was someone literally traveling with us home the whole way before we had to split off. There was always someone at the dinner table or bar. I don’t want to do it with his colleagues in earshot obviously! I don’t have his number, only work email.There’s a final event next week. Do I (1) wait til then to ask him out, (2)or email him tomorrow? Or (3) leave it as he doesn’t seem interested?
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