First time caller, long time listener.

TLDR: Semi-successful night out. Ventured on my own on a Sunday night. Met two girls, one definitely interested. They invited me to a club across town. Had great time. Light kino. She bought me a shot, asked for my number, wasn't down for a kiss.

[Background info. I'm 28 with an average body, maybe 10 lbs too much but slim muscular. I am fairly attractive (on the 'ridiculously cute' side) and in no ways concerned with whether a girl will find me good looking. I am new to the single scene after a looooooooong (7 years) absence. Have no problems approaching in the right situations or making conversations either.]

My Sunday was awful and I decided I needed some time to go out and have fun. I wasn't looking to get laid, just wanted to have a good time. I live in a spring break city in Florida, so there are good bars out there.

I walked around and checked out a few bars, but noticed either everyone was a couple paired up, or girls I just wasn't interested in talking to. I talked to one girl while her friend walked away waiting to order drinks, and while she told me her name and where she was from, she came across and very aloof and uninterested. The whole encounter was maybe a minute before I got bored and moved on.

I figured the scene was dead at about 11 and was heading home when I heard some killer live music across the street. I decided to check it out and grabbed a beer. As I was waiting I saw a cute redhead (aka E) looking at me a few times and smiling but turning away whenever I would make eye contact and smile back.

I got my beer and waited to see if she was with a guy. I noticed her sit down with a friend (aka K...as looked EXACTLY like Kat Dennings, it was uncanny) and start talking. I made my way around the bar and live band to check everything out and, finding nothing else uninteresting, decided these two would might be good company. I walked out to the balcony where they were seated at a picnic table setup:

Me: Is this seat taken?

K: (smiling at me) It will be in a second

I take a seat across from them and introduce myself. At this moment it's hard to hear since we are right here the band is right next to us. After some good conversation back and forth (I'm switching between talking to the two of them, K is the better talker and we get along better, but she's recently married). All the while I notice E is wanting some attention, so I engage her here and there to keep her from being bored but keep going back to K. Kino here has not been possible. Shortly after the bar has an early last call. I asked them for one more drink before leaving, but they can't.

E:We're going to (bar x) across town if you want to come

Me: (grinning nonchalantly) Only if you want me to come.

E&K: (glance at each other and back) Yeah!

I get to bar x, where I've never been, get a beer and meet up with them where they're playing darts. I haven't played in forever and don't know how to score, so I play the 'helpless card' and have E help me keep track. Interactions are going well, lots of smooth and natural conversations going on. Lightly touching E on the arm, back, grasping her hand first before the darts when she hands them to me. (I initially tried Kino with K before I realized she was married. She ignored it, I think for the sake of her friend more than anything).

At one point K was at the bar. E is asking my my age, telling my she thought I was 22, and I'm telling her about how I noticed her interest in me. A random guy is talking to K and I used it as an opportunity to talk to E.

Me: So is this what it looks like when K is trying to get free drinks?

E: No, she would be flicking her hair, jiggling her boobs (she is physically acting out what she's saying here), things like that.

Me: (laughing, start making strong eye contact) I had to ask. I've never bought a girl a drink before.

E: Seriously?

Me: Honest to God! I see too many girls use guys for drinks. I want to know if they are really interested in talking to me!

E: (sideways glance to K, thinking for a moment) I'm about to buy shots for me and K, do you want one?

Me: What are you getting?

E: (unintelligible)

Me: I have no idea what you said, but why not?

E buys the drinks and I continue having a great conversation with K. E comes back, we make up stupid toasts and drink. K walks towards the bar again and I gently grab the back of her neck, pull her in, and take the chance for a kiss. I get all cheek. I try again in case she thought I was trying to whisper to get but another shot down.

E: I'm sorry but I don't kiss someone I just met.

Me: Fair enough.

At this point I lost another chance as the lights came up and it was time to close. However, E asked me for my number and immediately texted me, checking to make sure I got it. I head to the bathroom and when I get back they say:

K: (playfully) Going in for a kiss with your hand on the neck is a little rough. You shouldn't be so rough!

E: (looking at K) I disagree. In a relationship it's great!

As we were walking out she tells me she doesn't kiss unless she is on an actual date.

E: Take me on a date and we will talk about that kiss.

I get in my car, they jump in a taxi and head out.

Observations:

Overall, I'm happy with the night. I had no expectations and had a great time. As for the learning experience, here's where I think I went wrong in the night.

  1. I wasn't willing to approach larger groups of women. Being alone I didn't feel it was worth my efforts, even if I was getting an IOI from one of the girls.

  2. I've never been a dancer and need to just get out on the floor. This is a weakness of mine that is in desperate need of attention.

  3. While I used Kino, I didn't necessarily escalate. I think this is why I failed at the kiss. It came out of nowhere to her.

  4. I was having awesome conversations with both of them but should have honed in on E more.

  5. Coming out of a LTR of 7 years, I was accustomed I grabbing my S.O. behind the head and pulling her in. She enjoyed me being forward, direct, and taking what I want. While I was in no way rough with E, I feel a different approach is in order next time I attempt a kiss.