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Yes — the group setting absolutely made it harder, especially because she was not alone and you were effectively entering an already-formed social circle.

But honestly, you handled it pretty well.

You did several things right: you approached naturally, you did not act creepy or overly intense, you engaged the whole group instead of laser-focusing only on her, and you exited politely. That matters. In a group, if you ignore everyone else and only try to isolate the attractive woman, it can feel socially aggressive. By smiling at the others and talking to the guy too, you lowered the pressure.

The guy inviting you to the running club is actually a good sign socially. It means the group did not perceive you as weird or threatening. They basically gave you a socially acceptable doorway into their circle: “Come to the Sunday event.” That is better than trying to force a one-on-one conversation with her on the street.

With the influencer woman specifically, the group made it difficult because she had an “audience.” When someone is with friends, especially if she is known online, she may be more guarded. She has to manage not just you, but how her friends perceive the interaction. A one-on-one setting gives more room for warmth, curiosity, teasing, and personal connection. A group setting often stays more general and performative.

The best move now is not to DM her directly with something too intense. Follow the running club page. Go to the event. Be social with everyone, including the guy who invited you. If she is there, greet her casually: “Hey, nice seeing you again — I actually came after your friend mentioned the running club.” Then do not hover. Let the connection breathe.

The key is this: treat the running club as a social ecosystem, not merely as a way to get to her. If you become familiar to the group, your chances of naturally talking to her one-on-one improve a lot. And even if nothing happens with her, you may meet other women and expand your social life.

So my read: the interaction was a win. You approached a pretty influencer in a group, did not get rejected harshly, got invited into a social event, and left with dignity. That is real social progress.

dale74 · M
Most celebrities in the influencer age are not worth your time
Heroisthebest25 · 22-25, M
@dale74 Yeah maybe but I was just being social. I am 25 now and done with University life so just trying to talk to new people and gain social skills and build new connections.
dale74 · M
@Heroisthebest25 good luck
MarkPaul · 26-30, M
Why don't you write about approaching an employment interviewer?

 
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