Dating someone you indirectly work with?

Hi,

I am working in a pretty big company and recently talked to my manager about some stuff, and the topic of dating came up.

Since the company has many people, dating itself is not as weird I guess, but most of our work is done for other companies. My manager pointed out that there are many couples inside the company which was sort of weird for me, because I really like to keep professional things professional. But the point is that dating seems to not be frowned upon. That intro is just there to show that I really don’t want to “poop where I eat” so to speak, but I am not really sure if my current situation falls into that category my manager talked about.

I am currently working on a project for a customer company with a lot of people, and indirectly worked together with a lady I fancied for quite some time, not romantically but as a person. I really enjoyed working with her, and she was sweet, fun and beautiful.

I didn’t really have contact with her directly, since she is basically my customer(so to speak), just meetings, mails and some memes with casual topics in private messages, but I never even thought about dating her.

One night, I met her in person, it was a team event of the project where I didn’t expect her to be at, tbh. At that time we haven’t had contact for about 3-4 months. I just came directly to her when I saw her and said her that I really was thankful for all the help she provided during that time we worked together, and that it was a real pleasure working with her. I went back to my seat(because there were like 100 people at that table having dinner after the event which I was obviously also at) and continued talking to the people in my direct team.

After people started to go home I sat myself at some other place to talk to a few other people. Than suddenly she sat next to me without any warning. I didn’t drink anything(thank god) so I saw her in full light and have everything burned into my mind. I was asking her all I ever wanted to ask on some personal topics she mentioned a few times and realized that she is more interesting than almost anyone I ever met. I spent the next 2-3 hours listening and now I literally can’t stop thinking about her(weeks have passed since then, still the same).

The negative sides here are that I believe she is out of my league financially(if I understood correctly, she is kinda wealthy) which is a turn off for me personally(sue me, I am old fashioned I guess), but everything beside that makes her such an interesting character to potentially date.

I have taken every excuse to contact her and I feel like shit because of that, because I really like my job and I would like to continue working on the project. I don’t know if she is single nor if she really is interested in me.

The worst thing is that I have literally postponed dating for my entire adult life. I have zero experience in relationships and would not want to humiliate myself or to risk my job. I waited for someone interesting to drop into my life and this seems to be the chance but I couldn’t be less prepared, and with it I am starting to talk myself out of it.

I have thought about just joining a few dating apps for the sake of it, but I don’t want to use people just to be more prepared for a women I don’t even know if she is at all interested in me or even single.

I am certain that this is overthinking, but if you have read until here, is this a valid fear about dating a customer/coworker?

We are going to have more contact in the next few months, but not as much as it used to be in my previous assignment, so she is my customer on paper only. We do work on the same big project and I don’t know if that is frowned upon?

What do you guys think?