It happened. It had to at some point. He didn’t show up. Jake, who I met on OkCupid. We wanted to meet for post-work drinks. Here I was at 7pm…7.05pm, 7.10pm, 7.15pm. I texted him through the App, but he didn’t read my message. I had to smile. I believe in energy and how when......

It was the last week of our 30 day competition. Pressure was on! I was again experimenting with little app-texting and going nearly straight to the date. More fun? After all, my shower-hair-makeup-ready routine was down to 40 minutes, and I’d save time not endlessly texting.  Owen and I had a good initial back and......

Valentina gave me a task for my 3rd date with Evan (read about our 2nd date here). She and I are on the opposite ends of the spectrum when it comes to assessing dates we truly like. She is driven by her brain, sharp, analytical, cautious, very good at pointing out potential challenges. I am......

I really thought “smart, nice, curious, adventurous” were my most important criteria. How does one explain the criteria for connection? For being drawn to someone’s personality? And wanting to see them again even if they don’t perfectly check the boxes? My reaction to this date still mystifies me. I really like Paul as a person.......

Sometimes I think I’m pretty clever. But from the second Quinn opened his mouth, I couldn’t for the life of me place his accent. Italian? “Nope.” Ah I know, it’s Argentinian! “Nope.” Ok, say something in Spanish. “Hola.” Oh you’re Spanish! The charming, quirky voice was an exact replica of Enigo Montoya (Mandy Patinkin!) from......

I’m not going for nice and stable. Not a huge new learning, but a good reminder. When I was 26 I broke up with my long-term boyfriend. Till today, he was the kindest and smartest boyfriend I’ve ever had. He was funny, extremely caring, interested in the world, successful (while still having a life!), wanted......

(Read first date: #7) This was Tom again, the financial inclusion CEO guy. The one I was super nervous about seeing the first time. The one who totally impressed me for 3.5 hours with his stories of travel and working in developing countries. It’s now been just over a week since the first date. No......

I was feeling behind on the challenge (only 10 dates after 19 days!), so I thought I’d try to fill my pipeline with less back-and-forth texting. Just as an experiment to see what happens! Rick’s Hinge profile was terse but it did say “human rights technologist,” and high-quality pictures showed a nice, respectful person. Good......

I’ve never been a quantity person. I applied to 4 universities and got into 4. My dating history has been few and far between. And yet, I’m seeing clear structural advantages in dating a high quantity of people – even for a person like me who prefers the quality approach. There’s good, strategic reason to......