I’m a 29yo brown guy with a man bun rocking a sweatshirt with a blazer and gold chain. Went out to this social event in Boston for people in their 20s/30s. Haven’t been out in 4 months cuz of life but finally pushed myself. Basically we pregame at a bar and then walk over to the club. (Full disclosure, I do mention the race of the people I interact with just for context).

Reconnected with the guy who runs it. Caught up on life for 10 min.

Random guy complimented my man bun. I complimented his hairstyle and we chatted bit.

Then I approached this group of 3 girls + 1 guy (all white) who were sitting at the bar. One of the girls was reading the menu so I asked her about it. We had a lil sarcastic banter and then she suggested a drink. I was talking to her but also gave my attention to the whole group. The other 2 girls looked at me like kinda taken aback and lil annoyed. Guy also looked at me a lil taken aback but then smiled when the sarcastic banter happened. After 5 min I felt like I overstayed my welcome and left saying “thanks, appreciate the drink suggestion” ✌️

Moved to another part of the bar. Ordered my drink. While waiting there this was cutie on my left so I complimented her tattoo. She replied thanks in a nonchalant way. I asked her about the guy she’s with and she replied “oh we’re just coworkers.” So I asked about her job. She works in the military and visiting from SoCal. I replied with “thanks for your service. Don’t know if you appreciate that or sick of hearing it.” She smiled and responded “Nah nah l appreciate it.” I wanted to keep the convo going but my drink came and she visibly turned her back to me to talk to her male coworker who she was here with. Took that as a sign that she didn’t wanna talk further.

Then as I was walking through the bar I noticed this interracial couple (white girl & black guy). Complimented the guy’s fit and the girl’s scarf. Talked about how it looks homemade and asked if she made it. She smiled and laughed saying “nah I’m not that creative lol but this was handmade I’ve had for years.” We all chatted and laughed a lot about how our fit game is strong and whatnot. During the convo I basically said I find interracial couples hot and got a kink where I love to voyeur couples if ya both are down (Full disclosure I know this was probably the wrong thing to say but it’s how I felt in the moment and wanted to just practice shamelessly expressing myself instead of just thinking about the right thing to say). They both laughed like they were flattered but shocked that I said that. The girl with a huge smile was literally falling into the guy’s chest almost like she felt nervous but also trying to hold in her laughter. She basically said “I mean…this is our first date so we’ll have to see how it goes.” Guy was holding onto her tight from behind, smiling and saying “I don’t know bro. Lol guess we’ll just have to see.” I said “I feel ya, want my number in case ya in the mood later?” They both smiled/laughed and replied “We good bro but thanks tho.” I said “No probs hope ya both have a fun night.”✌️

Then I chatted with this group of 3 white guys and 1 girl (black girl moved from Miami). Had a fun convo with all of them.

Then the whole group walked over to the club. Had a good convo with another group of guys. Talked with a couple older women who mentioned Bill Burr so I just chimed in on them and they were initially taken aback but then pretty receptive. Soon as we crossed the street they said “goodbye enjoy your night!”

In line for the club I spoke to this black girl. We had a long, deep convo about her life. Seemed super cool but also socially awkward; I didn’t really find her attractive and she spoke about her ex often so wasn’t feeling anything further with her. But I wanted to talk to everyone and liked how sincere our convo was.

Later in the club I reconnected with the black girl from Miami on the dance floor. No talk, just straight up dancing, grinding, vibing, feeling each other. We even ran into the interracial couple on the dance floor I approached earlier and we were eyeing each other like “hell yeah”. We danced for over a good hour; I bought us a round until I suggested we head back oto the bar so we can actually talk. She said yes and we did. We had a pretty good convo about life, cracking jokes and she was kinda cute but…….i didn’t really wanna pursue anything with her. Even when she gave me all these signs asking where I live and “ooh your place seems nice” and lotta leg touching I just….i just thought back to all the other girls I saw this night and how I wanted to be with them instead (including that white girl with the black guy). I walked her back to her car, she even offered to have me join her in the car while I wait for my uber but I said I’ll just head back to the bar and wait (I also just wanted to hit up the strip club). We exchanged numbers, a kiss and left it at that.

Went to the strip club later and then ubered home.

Welcome any insight y’all have into my approaches/convos (DMs open). Nothing to brag about here but wanted to take those brave baby steps to build on. Lemme know if ya got questions or need clarity.