Y: So how are you on the relationship front?

P: Well it’s X and Y.

Y: Doesn’t that make you {emotion}? I hate/love it when X and Y. It/they always {observation}

P: How are you?

Y: Oh you know, still lookin around. Easy to meet girls but hard for me specifically to meet the girls that I’m really interested in dating.

P: What kinds of girls are you interested in?

Y: I would love to date a med student or a grad student honestly. I think I’m attracted to intelligence and also the idea of pursuing goals beyond just subsistence. Right? independent thinkers. And honestly vicariously it’s good for me because I always loved academics and learning. But I don’t think I’ll ever go back now.

P: I’m surprised it hasn’t worked out.

Y: Yeah it’s alright. I think I’ve identified basically 2 challenges that I have in starting relationships

P: Yeah? What’re those?

Y: Well for one, I lack subtlety. When you’re in that puzzle phase of trying to figure out, “does this person like me?” It’s all about sending out feelers. Not direct feelers though. Why. Because if you’re wrong, you save yourself embarrassment. You’ve spent less social capital. In the old days if you went after a partner and were rejected, you got kicked out of the tribe. Subtlety allows you to stay in the tribe.

P: Okay

Y: Now take this girl I know. I think she likes me. She knows how to be subtle. She keeps saying things like, “yeah I always date boys in finance because x and y.” X and Y being attractive attributes of boys in finance. I work in finance. You see? Indirect expression of interest plus an indirect compliment. Now take me – I am literally so not subtle that I wrote a letter. Probably a good 400 words to a girl I had a crush on. What do you think happened? Total shut down. Granted, she lived in a different city and hadn’t talked for years but that was different.

P: That’s not so bad. At least you tried. That’s more on the girl than you.

Y: I appreciate you saying that.

P: Well what’s the other one?

Y: The other challenge? It’s just lack of experience. I think I know when I like a girl but I don’t have a ton of experience so… you kind of have to answer two questions right: you gotta figure out through subtle means – does she like me? and also you gotta look at yourself and say “do I like her?” And I know when I like a person. I just don’t know yet when I like a person enough that a relationship is going to work.

P: I see. Well just to be clear, I don’t give a damn about you.

Y: Really? Damn. Alright….

P: Alright.

Y: Hey! How’s it goin?

P: Good!

Y: Good… Are you surprised that I called?

P: …

Y: Reason I’m calling is again, honesty and transparency… I want to make sure that you don’t feel like I’m hiding or anything. Or that you can’t talk to me or be honest. I wonder what I can share that will help you the most but maybe from the top it would just be my intentions.. where I’m at. Is that helpful?

P: Yeah

Y: So my intentions hopefully are pretty clear… which are that I enjoyed talking to you at the food festival, would love to get to know you better… in general, I’m attracted to intelligent girls, girls pursuing higher education. But I want to be respectful of your relationship and what you want.

And so all of our hangouts since have been as friends. I THINK that you’re on the same page there and you’re doing a great job of striking the right balance. You mentioned that you were hoping to work things out, then you brought friends to the jazz concert and we didn’t meet up at HSB.

I think all of that was handled well. Do you agree with that – are we on the same page?

P: Yes

Y: Okay. So that then kind of leads to where we are as friends. I unfortunately don’t have a great answer and that’s maybe what this conversation is about. My story with my McKinsey colleague illustrates, at least in my mind, is that this situation is tricky.

Like at a basic level, you’re all the way in Oakland, so if I reach out to hang out as friends, it has to be very intentional and planned. And maybe that comes across a different way and maybe we’re back onto different pages. You see what I mean? So with my McKinsey friend, I initially tried to date this girl, then I was just trying to be friends, and unfortunately the friends phase (because I guess it felt intentional to her and she was then single) was interpreted totally incorrectly.

If you have ideas, I’m genuinely happy to move forward on whatever basis you like. I’ve been trying to think of situations to hang out but unfortunately either I’ve been traveling, you’ve been traveling or they haven’t been there without intentionality. I mean maybe we put a “No this is not a date” disclaimer on all of our plans to hang out.

P: (The answer)



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