I’m splitting this post up into 2 parts – one for each pick up. The second part is here.

I went running yesterday in the park. It was an early Friday evening, the sun was shining and I was just trying to relax and get some exercise. I was a little nervous about picking someone up – I don’t want to put too much pressure on myself for having to try and pick someone up every time I go running, but at the same time I don’t want to get lazy and not take any chances. So I decided I was going to be friendly and say hello to everyone I passed and if I happened to pass a woman I wanted to talk to, I’d just let my sub-conscious take over and see what happens.

As I was saying hi to people I passed by I could feel myself loosening up socially and feeling like I can actually approach a woman – I feel these warm ups are really important, which is why I’m continuing to do my daily morning pick up practice.

About a third of the way into my run, I see a couple of attractive women walking from another path and getting ready to merge with my path. But since they’re not passing directly in front of me, I feel too awkward to just stop and start talking to them. I rationalize to myself that when I turn around, I’ll run into them again and then I’ll start talking to them.

I continue running and a few minutes later I see 2 women and a guy walking. Both women are quite attractive. All 3 are wearing business attire. One of the women has a sexy business skirt with a red dress shirt while the other is wearing quite flattering business pants and also a red shirt. This is kind of a strange site in a park. I don’t feel confident enough to just stop and start talking to them but I manage to say, “Isn’t this kind of formal for the park?” as I’m running by them. Both women laugh and one of them says “We’re taking a walk after work.” I smile back at them and continue running. I reach my halfway point and turn around.

I’m getting ready to see the 2 women walking together that I totally passed by without saying a word. But they’re nowhere to be found. I’m feeling a little down but somewhat relieved that I didn’t have to take another chance with a new woman (old fears die hard). And then I spot the 2 women and 1 guy walking up ahead! I’m running towards them and I start thinking: The women seemed friendly and open – let’s just see what happens.

As I run up beside them I just stop running and start walking with them. I open with something like “Hi! So I just had to find out more about you guys. It’s not everyday you see people dressed this way in the park.” The women and guy all smile and respond warmly and the 4 of us continue walking together. I make some joke about how the 2 women are both wearing red and if they planned that. They both laugh and say how they didn’t mean to wear the same color to work that day and I just joke that I thought women have this 6th sense about fashion and always wearing something unique from other women, so maybe their sensors are broken or something. They laugh and I can feel their friendliness and openness. Turns out they all work at the same company and they regularly come to the park for walks. They ask me how often I run in the park and at what time and then one of them says that they should come walking in the park at a time that coincides with me running there.

All 3 of them have a slight accent and I recognize it as my native language, so I ask if they’re from that country and they say they are. I tell them I am, too, but they’re surprised to hear that because I don’t have an accent. I introduce myself and they tell me their names – Jennifer, Tanya and Steve. Both Jennifer and Tanya are very attractive but I notice that Jennifer is friendlier while Tanya is more quiet. Steve also seems friendly and he starts asking me questions about what I do and it turns out we have stuff in common with what he’s working on. I didn’t want this to become a shop talk session so after a minute of shop talk with Steve I bring the focus back on Jennifer and Tanya by making a joke about how they’re the big techies in their company (which they didn’t strike me that they were). They both laugh and we start talking about their background and education.

We must have walked together for about 10 minutes and eventually come to a fork in the road – they’re going one way while I’m going the other. Steve hands out his business card and gives it to me because he thinks we could possibly work together in the future and to stay in touch. I tell them that it was nice meeting them and that it would be great to run into them in the park again.

And then I decide to go for it.

I say to Jennifer: “Listen, I don’t know if I’ll run into you here again, so instead of waiting for that possible chance, I figured I’d just ask you right now if you’d like to go out sometime.” Jennifer smiles and giggles and looks at Tanya and Steve, who are both smiling and giggling. I’m just standing there with a smile on my face, too, knowing that I’ve probably given them something to talk about after we’ll part ways in a few minutes. I add, “I’m not really sure what the dynamics of all of you are – I don’t know if Steve is with you but I thought I’d ask anyway.” Then Steve tells me that he’s not with Jennifer and that he’s Tanya’s brother. Great! So now Steve is actually helping me out by implying that Jennifer is single and available.

Jennifer replies with “Why don’t you call my company and we’ll take it from there. You have Steve’s business card so call and ask for me.” I say “Great, I’ll do that.” and wish them a great weekend as I tuck away Steve’s business card into my running pouch.

I continue running for home and say hi to almost everyone I pass. What a great start to the weekend! But I didn’t know that I was going to pick up someone else that day, too. I’ll post that tomorrow.

Things I Learned

  • Ask out the one woman I’m interested in and not both at the same time. Unlike my last pick up attempt, where I asked out both women at the same time, this time I asked out Jennifer explicitly so it was clear I was interested only in her.
  • Talk to everyone in the group. I’ve been doing this already, but it’s still worth mentioning. I talked with all 3 people in the group so I came off as friendly instead of like some stalker dude who was only focusing on the one woman and ignoring everyone else.
  • Don’t get sidetracked into shop talking with the guy. I could have easily continued talking shop with Steve, but that would have ruined my chances of building a connection with Jennifer. So I made sure to change the subject quickly and refocus on including the 2 women in our conversation.
  • Smile and stay upbeat as I’m asking her out. I think it shows gutsiness and that I’m going after her without any excuses – but in a respectful way. I like how I feel afterwards and I think women appreciate it, too. I think women like to be asked out by confident, gutsy guys.