Hello people of Reddit, I am new here and this will be my first post. I basically chose this as a place to write out some stuff I am struggling with.

First some information about me: I am a 35 year old man, my wife and I got divorced 9 months ago after being together for 12 years. We have one daughter together who is 5.

It was a huge blow for me when my wife left and I have been going through all kinds of emotions since. I’m not sure I’ve worked through it all yet, but a couple of weeks ago I met someone who I can only describe as the most beautiful woman I’ve ever seen. Meeting her kind of rekindled a desire for a relationship. We met because she occasionaly drops stuff off at my new job where I started last month. My team handles deliveries so whenever she comes by we’re the ones she deals with. She’s very nice to us, but she doesn’t hang around and I haven’t talked to her about anything other than work so far, but if I should decide to pursue this, I guess I’ll have a shot when she comes by again.
I have some issues though.
First of all, I’m not sure I’m ready for a new relationship. I don’t want to set us up for failure simply by doing this too soon. But I also don’t want to lose my shot with her by waiting too long to make a move…
Second, I have no idea how I would go about this at all. Walking up to a stranger and steering the conversation towards dating is a skill I never developed, and even if I did, last time I’d have used it would be over a decade ago.
Third, should I even try this, considering the professional connection, however tangential? To be clear, she is not a co-worker but still she comes by like once every two weeks. I don’t want to make it awkward for anyone when she does.
Fourth, after a couple of rough months in the love department, seeing her and looking forward to seeing her are the best feelings I’ve had for a while. A small part of me wants to keep those feelings and not ruin them with knowing she’s not available or interested in me.
Fifth, a much bigger part of me does want to know because when I think about this situation, I find it weird. I mean, so far I’ve seen this woman 10 minutes tops and I know nothing about her except her name and where she works. And I still can’t get her out of my head… If it can’t happen I’d rather know so I can move on and stop this madness. But that just brings me back to “how to find out without making things awkward?”

This post went on for longer than I expected so thanks for reading through it all. And thanks in advance for any helpful advice.
And to the moderators: If this isn’t the right place for my post, feel free to move it, just tell me where it went so I can find it again 🙂

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