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This approach happened before I changed my dating strategy.

While I was running in the park, I bumped into Heather, the woman I approached the other week while running. She was walking with a group of people – looked like she was doing another training session with them. I said hi to her and her group and we talked for a few seconds. There were four of them all together. Three women and a guy. The guy didn’t look like he was with Heather and it turned out one of the women was his sister.

I didn’t stop and interact with Heather further and just continued running. Now that I’m thinking about it, I can’t help but kick myself for not pursuing her further – I could have said something like “So when can I run into you again?” and see if I could get another time we could talk further.

On the way home, I noticed this woman walking ahead of me on the sidewalk (away from me). She looked really good from behind as I was approaching her but when I turned around, she wasn’t as attractive as I had hoped (5). Doesn’t matter – by then I had made the decision I was going to go for it (like one of those missiles that’s been fired – once it’s fired, you can’t bring it back).

I say hello as I pass her – in a friendly way.

I run to about 10 feet ahead of her, stop, turn around and say, “How are you?” – still being friendly and upbeat.

“Fine.” I thought I detected an accent – maybe English isn’t her first language.

I go into my banter – something I thought of trying previously:

“I’m doing a survey for the city, and we’re talking to all the beautiful citizens of our city to find out how we can improve our streets.”

She’s not quite sure whether to play along or if I’m serious. She doesn’t answer much at first and I thought I would have to jettison this approach pretty quickly. But then she starts talking and we get a conversation going. I ask her what she does and how long she’s been in the country. Turns out she’s a caregiver for a family and has lived here for four years. I ask her if she has a husband (I don’t know why, but she seems like the type to have a husband) and she says she doesn’t. So then I start joking with her that in addition to my other 2 jobs (running and taking surveys for the city), I’m willing to take on the task of finding her a husband. We have a great time laughing about this and I feel I’ve made a real connection.

After about 5 minutes of walking with her, I decide it’s time for me to run home so I tell her it was great to meet her and wish her all the best.

I continue running for home and spot a really attractive woman walking up ahead of me with a baby stroller. I’m approaching her from behind so I try and be really easy going, so as not to startle her. It works, she responds very warmly to my “hi”. I then ask, “Is that your baby?” (I wanted to be really sure that she was unavailable, OK?!) and she says that it is. I then say, “She’s really lucky to have you as a mother.” The woman smiles really genuinely and I can see that I probably made her day. That felt good! And I didn’t even ask her out. I like making women feel good!

When I get very close to my building I spot an elderly woman. I’ve started to do my cool-down walk by this time and as I pass her (she’s walking in the same direction as me) I say a warm hello and ask her how she is. She answers very warmly and I somehow get into a conversation with this woman (I’d say she’s in her 80s). She’s funny, too! One of the first things she tells me is, “I’m too young for you.” I’m bantering with an octogenarian! Hilarious! We end up having this really great talk for the next 10 minutes – she gives me all this advice about what kind of woman to look for. How the woman has to have her own career and know how to work and not just depend on me to give her money (all things I agree with but it was nice to hear this coming from someone a lot older than me).

I’m genuinely grateful that someone a lot older and wiser is sharing with me their wisdom. At the end, she thanks me for stopping to talk to her and tells me how it’s not often people of my age stop and talk with people of her age. I thank her for sharing her wisdom and I go home feeling great.

Things I Learned

  • It’s not about pick ups – it’s about making connections with people. I’ve had numerous interactions like this that I haven’t blogged about – spontaneous conversations with people that I had no interest in picking up. But it was a worthwhile interaction and rounds out my social skills.
  • Banter is a great way to see if a woman has a sense of humor. The woman I approached wasn’t a native English speaker but because we were bantering, it made it easier to connect with her and to see that she was someone fun.

List of All My Pick Up Approaches


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