I've been going out to bars on the weekend the last few weeks. It seems like when I'm out I strike up a conversation with a random guy, and end up having a great conversation. I just talked yesterday to this guy from Tunisia, a great guy and funny. Only problem is I went out with the intention of talking with women, so in a sense the night was a "failure" (although I don't count any night as a failure as long as I had a good time).
I think I use these conversations as a bit of a safety blanket to not have to approach. I think in the future, I'll still strike up a conversation to get me feeling more social and at ease, but cut it short a bit if I see a girl that I want to talk to. There was a girl at the bar standing by herself and kind of flicking her hair that I wish I had talked to, so next time I'll just excuse myself and go talk to her. I don't want to be rude to the guy I just met, but that is why I went out, really.
Also, the first person I talked to was a girl at the bar, so that was a positive step. She was laughing and stuff when we talked, I think I could have escalated with her, but instead went to go get a drink and she said "okay, nice meeting you", I thought I had more time, but all good.
Overall, I feel more comfortable going out by myself and I tend to have a good time, I usually meet at least one interesting person, even though a lot of people aren't that comfortable interacting with a random dude like me (that's just people). I think flexing those rejection muscles is really important to being able to have a good time out by yourself.
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