First Date with an Old Co-Worker/Friend

[artsyfartsy32]

Full disclosure- I haven't dated for 5 years- I am newly single and have recently asked an old Co-Worker out, the "date"(?) is tomorrow and I'm super nervous.

I haven’t seen this person in 3 years and when we worked together we I was in a committed relationship, so the notion of dating never came up… I did, however, develop a small crush on him just because we had SO much in common and he was absolutely hilarious, even though I wasn’t initially attracted to him physically, he sort of grew on me. My ex is a very jealous person and he forbade us to be friends and I complied, much as it saddened me to lose my friend.. I’m no longer at that job and neither is he, we haven’t spoken in 3 years. 3 months ago I caught my boyfriend of 5 years cheating on me and we have since ended things. We have a 7 year old daughter (it was an on again-off again sort of thing) together so dating is especially scary for me because I need to be incredibly picky about who I decide to bring into my life. I haven’t really put any thought into dating at all.... However...There is an obscure movie that I want to see and I remembered a conversation i had with said co-worker long ago about the prequel to it and thought ‘Why not?” thought it would be a good segue into meeting up with him and seeing if maybe there had ever been something there. So I asked him to go and he agreed, but I really never said that I was single now, it just felt awkward to bring it up first thing and I didn't want to sound, for lack of a better term, "thirsty" lol. I feel like my intent might be implied, or he just might be completely oblivious, I really can't tell. I am concerned that he’ll read this as just a friendly outing and nothing more- how do I navigate this awkward situation? I kind of want to up front with my intentions without coming off as creepy and saying "Ermagherd I used to have a massive crush on you, heheheh, but I'm single now..eh???" *awkward finger guns* or something to that effect, haha. I don't want to risk losing the possibility of rekindling our friendship, either. Did I mention I used to technically be his supervisor? LMAO maybe the inappropriate factor is a turn on for me. He's a little older than me but I'm into it, I honestly want to find someone 5-10 years older than me anyway, (no offense, young dudes) I feel like I need a higher maturity level than what I'm used to from a man. Also, not to toot my own horn but I do not think I am too terribly bad looking, I'm unconventionally attractive in an interesting way. Like Emma Stone or Kat Dennings, lol. He's not the hottest dude in the world but I really dig his personality and we never ran out of stuff to talk about. What I'm saying is- I'm confident... but this dude makes me nervous and I don't want him to know it, lol. I'm asking you fellas because I feel like you'll be honest.... Your advice is appreciated!!