Most appropriate way to ask out a friend from work?

[Anonymous]

I just want to preface that she first asked me out a couple of months ago after she went through a breakup. We had a great night together but her breakup was too fresh as was mine so we didn't forward. We're both in our 30s. We're more friends than coworkers and we have like 8 employees

She has been flirting and talking a lot lately and seems in a better place, I feel like I am too and want to officially ask her out on a date, see if the magic we saw that night becomes something. I'm just not sure when/how to do it. Like definitely not inside our workplace, at times we hang out after work or outside sometimes, usually at her behest. I should probably wait for her to suggest something outside before asking her right? Or when I'm taking her home. Her breakup was two months ago, mine 4 months ago, you think she's ready to be asked out based on how she's acting? She always wants to be at home with her cats whenever she's not working

[exitseven]

Since you have a little bit os a history already it should be a pretty straight forward process. Just come right out and ask. It doesn't have to be anything big just dinner maybe.

[Asker]

I just don't know when to ask her, like today at work we talked a lot but seems kinda weird to ask her there. We meet outside sometimes when it'd be better but today we didn't. Sometimes I walk her home but she hasn't asked me in a week. The moment is never right and I don't wanna lose her :l

[exitseven]

I don;t know if there is ever a "right" moment. Sometimes you have to just hold your breath and just go for it. Like I said, you already have a little bit of history so it should not be a total surprise.

[Asker]

Yeah I'm sure she knows I like her because ever since she invited me out I've been more around her and open with her, even suggesting things she had said we should do. I don't know if it's her breakup or what but she's been hesitant about doing anything together but still talks and flirts with me a lot, which is why I want to ask her on a date to make it clear. But yeah there might never be a right moment. I just don't want to do it in our office building that's for sure

Either that or ask her why she doesn't want to ever do anything together but that seems more confrontational and not the vibe I'm going for. I think I'll just wait until she suggests something, at least wait till she asks me to walk her home

[Anonymous]

Just say, hey, would you like to have lunch one day this week?

[Asker]

I did that about a month ago and she said yeah but then cancelled. She still continued to talk to and flirt with me the next time we saw each other so I don't know if she wants to be asked on a date or what

[Opinion Owner]

Ok, ask him one more time but that’s it.

[Asker]

But I should specify it's a date right?

[Opinion Owner]

No not necessarily.