As I’m running through the park, I spot an attractive woman walking by herself in my direction. This would be a perfect approach opportunity. But I hesitate and don’t stop. Damn it!

As I’m kicking myself for not stopping, this really cute Asian woman (7) starts running next to me from an adjoining path. She just happened to have started running at the time that I was passing her. I just said the first thing that came to my mind:

“You going to run with me?”
It was a fun, playful thing to say.

She replies with “Sure, why not.”

She was wearing an iPod but takes it off the headphones so we can talk. We continue running together through the park. I start bantering with her. I’ve never done this WHILE running. Usually I stop to talk to women that are walking.

She tells me she hasn’t run for a year and I tell her she looks very good for someone that’s supposedly out of shape. I find it easy to put in compliments like this while we’re bantering – it just flows more naturally.

I joke with her some more – role playing that she’s my trainer and I’m the one that needs help with my running. I even mock myself by starting to run as if I’m very old and she laughs.

She tells me she’s new to the area and only lives five minutes away. I joke with her that I’m going to give her a fabulous tour of the neighborhood and that my limo is parked where she started her run. She asks if there’s any champagne inside and I say “Of course.” I ask her if she likes caviar and then ask her if she prefers red or black. We just have fun laughing and joking around with silly topics like this while we’re running and it’s just a great way to spend the afternoon.

We stop to rest a few times and we end up talking more, getting a chance to connect further. She even agrees to run with me past the point where she started. At one point I thought she suggested that she run with me all the way back to my building but then when we get to the end of the park she says she’d better stay in the park. I make no big deal about – no whining, no convincing her to keep running home with me. I just say “no problem” and we rest for a few minutes and talk some more.

Finally I tell her it was great to meet her and start to get ready to run for home. I can sense some hesitation in her voice as we’re saying good-bye. I think she was wondering if I was going to ask her out or not. But I decide no to. I wasn’t as attracted to her as I would have liked. Also, this might sound shallow but it’s true – she was a 7 and I want to date 8 or higher.

Things I Learned

  • Focus on bantering and having fun instead of asking her out. By doing that a few interesting things happened – she introduced herself to me, she wanted to keep running with me, she wanted to take breaks with me. We were having a great time and there was no pressure committing to a date or giving me her phone number. She felt comfortable doing all these things because we were both having fun – that’s it.
  • Not asking her out made me feel really empowered. Just because she was attractive didn’t mean that I automatically wanted to go out with her. It would have been very easy to ask her out at the end of our interaction and I think she would have said yes. But it’s more important for me right now to get more comfortable meeting and building connections with women than dating. This might sound strange, but I feel I’m too busy improving my approaches with women to worry about dating right now. This is not a permanent condition.

List of All My Pick Up Approaches