Hey y’all! I could legit use some help and I’d be glad to take any advice!!

So long story short, there’s this girl (F/23-25ish) that I’m kinda sorta friends with who used to be a coworker of mine a few years ago (I left the job in 2017, she left sometime after). As far as I know, she’s single and of course beautiful. From what I can tell, she takes care of herself.

My thing is I’m a guy at 27y/o and have a sum total of like maybe 2 girlfriends. First was in 2018 who I met online and after 3 months of long distance talking, she virtually stopped replying to any and all attempts of communication & ended up blocking me w/o any reason. Straight ghost. Second was last year in May & she broke up with me via text after 3 weeks of dating cause her mom said “I was too nice!” Outside of that, it’s always been “we’re just friends/I like you as a friend” or “I’m not looking to date right now” (then gets a boyfriend a week or two later) or they’ll play with me and act like they’re interested until they find someone then just leave me hanging. This last spring in “Early Covid” I’ve even met people online and made plans with them then within a few days of the date or day we planned they’d make something up like “oh, I can’t because Covid/work/something came up/etc” and I never got anywhere.

Needless to say, My dating life has sucked. Straight garbage. Dumpster fire. All I’ve done is try and then see what I did wrong and change it, but hasn’t seemed to work yet. After building some confidence (of which I lacked SEVERELY growing up) and fighting through the BS known as ‘my life’ and learning some on females, I’ve developed a small “I don’t care as much” vibe so I’m almost not as nervous SOMETIMES.

I’m also terrible at reading girls for the most part, probs in part cause I’ve had virtually no dating experience and I haven’t had any consistent interaction with attractive single women for the last 6-8 years or so outside of maybe work, lol. I’m also a virgin @ 27 if that helps give an idea of my luck with women or belief system. It could go either way, I don’t really care at this point, and I’d generally wait until marriage unless someone absolutely blows me away or if it just feels right.

Here’s my thing, the main point. Ive sent a few basic messages to this old coworker of mine via FB or Snap the past few weeks (nothing to much, no ‘real’ convos) but I finally decided to just shoot my shot and get an answer tonight and I asked her if she wanted to grab some food after she got back into town from her trip. She said yes she’s definitely down, she’s just got a busy schedule right when she gets back but did say she’d be down when we can find the time for it. I’m kind of excited & hopeful, but at the same time (unfortunately?) not expecting much to come from it given my luck in the past. She’s absolutely beautiful, pretty sweet/kind from what I remember, smiles a bunch & kinda sorta bubbly which I like, etc. I’m not sure if she’d consider it a “date” or not but I’d like some advice on what to do or how to go about it for the best results. The original idea was getting some food when she gets back, but I’m open for other ideas or even just down to the basic interactions between us. I’d like to get the chance to go out with her at least a few times if possible & see how far it goes, and if I can get far enough or long enough (ie a few dates, some kinda special connection/touching, etc) that’d be awesome.

I just don’t get out much cause of my current job I’m trying to get out of cause I’m literally always working 4pm-1am or 12pm-10 or 11pm & etc, and I’d love to finally have a chance at having even a slightly successful “dating experience” with someone beautiful for once in my damn life.

Sorry for the long post, and I’m not sure if the girl here even has a Reddit so I guess we shall see what happens lol

Edit: I Recently asked her what her schedule was like for the next week or two since she said she’d be a little busy once she got back in town. And well, as my luck has it she decided to effectively cancel any plans saying, “hey yeah, I’m not looking for any kind of relationship or anything close to that right now. So i don’t think that meeting up for food would be a good idea. Sorry.”