After the last pickup attempt while running, I was feeling pretty good – more friendly and social. I was saying hi to most of the people I would pass as I ran by them – men, women, children, senior citizens, whoever.

As I continue running towards the park, I spot a really attractive woman (late teens to early 20s) walking by herself on the sidewalk. I’m running towards her and I’m thinking this could be another chance to practice. Now, she’s dressed in her Sunday best, but it’s Saturday so it’s obvious she’s on her way to the synagogue. And I’m also pretty sure she’s been brought up to not talk with strangers on the street. Ah, what the hell, I go for it anyway…

As I run up close enough to start a conversation I stop running and tell her “Hi! I just wanted to stop and say hi and talk to you.” I think I might have said something about her looking interesting (I keep using that “interesting” adjective because I’m too chicken to say “attractive” or “sexy” or “hot”). She smiles awkwardly and looks down. She’s not saying much or giving me any strong indicators of interest so I just awkwardly say “But it looks like you’re on your way to shul [synagogue] so you probably can’t talk now.” She nods her head and starts to resume her walk in the other direction. I just bid her farewell and wish her a Good Shabbos [Good Sabbath] and she says thanks and walks away.

I felt pretty good after that interaction, as well. Mainly, because I did something that I was too nervous to do before – start a conversation with a woman while running.

I had a great run and said hi to most people I passed. At this point, it just doesn’t matter what reaction or result I get from each interaction. It’s just the act of doing each pick up attempt that makes me feel more social, relaxed and upbeat. I was feeling so good that I even tried to pick up another woman at the Starbucks coffee shop at the end of my run…

Things I learned

  • Stay upbeat. The more positive I am, the more chance she’ll feel at ease. After all, it’s a little weird to have some stranger stop you in the middle of the street and start talking to you. So if I exude a positive, warm, upbeat attitude, that’ll help put women more at ease.
  • Don’t give up so easily. I basically rejected myself by saying “you probably can’t talk right now anyway because you’re busy going to shul.” It gave her a very obvious way to get out of the interaction. I’m finding that it’s hard to keep an interaction going if you don’t get positive signals from the woman. But I’m wondering if that’s just women’s instinctual reaction because I’m just some stranger. If I hung in there and continued to talk to her, maybe some women would let their walls down.