I [24,M] have been going to the same bar semi regularly, enough to where the bartenders know my face. It’s a rooftop bar in my city’s downtown and a lot of young professionals go there. I try to go once a week or so just to “put in the reps” as it were to become more confident in my approaches, become a better conversationalist, and to get better with rejection. Here are some of the experiences I’ve had over the last 2 weeks.

3/30

Approached a woman with a green top and opened with “you know St. Patrick’s day was 2 weeks ago.” Lead to a good conversation about her city, Charleston. She mentioned in conversation she had a boyfriend and after a few minutes I wrapped it up and moved on.

Approached a group of 3 women standing near a heater. I complimented the one I was most interested in on her Trench Coat to open and spoke to the group about their work. They were from NY in town for the next 3 weeks to do a documentary podcast type thing. Got the Insta of the girl I approached. Messaged the next day with no response.

4/5

Approached 2 women by joining in their conversation with the bartender about “hall passes” and celeb crushes. They mentioned their boyfriends and I didn’t persue further, though it was a fun chat.

Was approached by an older (late 40s) woman and I opened with a joke about feminism. She was “complaining” about buying her male coworker a drink. I replied with “hey, yall are the ones who asked for equal rights.” She laughed and we had a good talk about my home town, as she recently moved there, our work, and the play I’m directing. We exchanged contact info, though I wouldn’t be interested in a relationship due to the age gap.

Approached 3 women who sat next to me. Tried to start up a convo about the Iowa game that we were watching but it was kinda clear that one of them were interested. I didn’t press, and left for the night.

Even though nothing has really come out of it yet, I definitely feel like I’m getting more competent socially and flirting is coming a little more naturally. I’ve also had fun just going out and talking to new people without any expectations. It’s just a numbers game at this point. Thoughts?