A few weeks ago I was bar hopping downtown and saw a really cute girl standing outside on her own as we were passing by. I stopped and chatted with her for what couldn’t have been more than 5 minutes. I opened up by complimenting her on her flannel top and told her I love it when girls wear flannel. She thanked me and told me she was there for her friends’ bachelorette party but got separated from them and was just waiting for her ride home.

From there we just made drunken small talk about nothing too out of the ordinary – what went on tonight, school, work, friends etc. We were both pretty drunk so the details are a little hazy but if I applied any kino it wasn’t too much, just a hand on the shoulder or light touch of the hand. I asked her if I can have her number and she says

Her: “Hmmmmm…I don’t know…”

Me: “Is it just because you are too drunk to remember me?”

Her: “Haha probably”

Me: “Why don’t I send you a picture of myself, that way you will remember whose number you got, and I’ll take your picture for the same reason” (CRINGE)

She agrees and she actually lets me take her picture and I send her one of me. I text her a little bit shortly after saying I hope she gets home ok and she told me not to worry since her step dad came to pick her up and he’s a cop. I say “woah so should I be afraid to ask you out then? :p” and she said “haha nawww he’s super nice” So I’ve set the tone with her now she knows I want to ask her out.

We text a bit the following Tuesday ( I limited my texts basically to just logistics), I ask her to get coffee with me later in the week. She replied with “hey its nice to hear from you!” but she informed me she’s leaving for a camping trip the following morning. I wait another week and text her again asking how the camping went – she didn’t answer. She never did seem overly receptive of me in person or in text so I just mentally moved on and sent one last hailmary text on Thursday inviting her to my bands show and then out to a pub afterwards on Saturday.

She took a day to respond but once she did she seemed interested and was asking for details. I let her know it was at time at church (not sure why it was at a church, I don’t do the booking). She however she seemed flaky about whether she’d make it out or not, saying “oh I don’t know what my friend wants to do yet” so I had zero expectations of her showing up and didn’t really expect to hear from her again.

I must have got her thinking about me though because on the day of the show she texts me asking “So what kind of event is this that you are playing in a church?”, I respond by saying “To make up for what we are gonna do tonight” and she responds “Lmao that’s good enough reason for me”. This is the first time I start to actually think I may have a shot.

She comes to our show and we were gonna meet up at the pub later but I took too long lugging gear home etc so we set up a coffee date for later in the week.

The coffee date was last night. I feel like this is the first time I’ve actually seen her when I’m sober so it was a little awkward at first. I hug her when she arrives and tell her she looks great. We order our beverages and I lead her to a table outside, but when I sit down, she sits across from me rather than beside me (wish I would have challenged her to sit beside me – I could tell she was just a bit shy). So zero kino during coffee. I just make sure I lean back and try to be as aloof as possible and maintain strong eye contact which she would break before I did.

She talked. A LOT. I feel like this is the most cool I’ve played it on a date in a long time. Oh I should mention that she’s 19 and I’m 25 so I kinda had the confidence that I know more about going on dates than her.

After coffee we go on about an hour long walk. We talk about our up bringing a bit. Turns out we went to the same high school, just 5 years apart. So we were able to bond over those kind of memories. And I actually found out we have more in common than I originally would have thought. She’s trying to teach herself how to play guitar and snowboard. As someone who taught myself those skills I LOVE hearing this. She complains about her job and I apply some of the only kino I could muster up by lighty slapping her shoulder when teasing her about work and pretending to stumble into her.

At the end of the date we chat by our cars for a few minutes and a little bit of tension builds but I know I’m not going to kiss her because I don’t feel I built enough attraction with her. So we hug goodbye and I fully expected that I probably wouldn’t hear from her again unless I did the initiation. But I got a text from her when I got home saying, “I had fun tonight! Thanks for not letting me stay home alone!” We text for a bit and then say our goodnights.

Pros: We got some decent rapport going by bonding over mutual interests and upbringings, had a few laughs, I was chill and relaxed and let her do a lot of the talking, broke down the awkward “first time hanging out sober barrier”. Another pro is that I stressed the fact that I wanted to ask her out from the onset of meeting her, which is an improvement for me cause often I just get a girls number and she doesn't know my intentions so its a bit awkward when I do try to text them later on.

Cons: Very minimal flirting and kino, and that’s it but I realize that’s EVERYTHING

She’s at the lake this weekend so if I don’t hear from her by mid next week I’ll give her a shout and see if she wants to get together again. I think in a more social setting and with a drink or two in us, along with a bit more comfortability of knowing each other a bit better I think something can happen.

I know I probably should have just manned up and went for kiss, but other than that…any pointers / critiques?