I was realllly nervous. Really really nervous. This was my first real “blind date” in the 30d30d saga. Yes, I mean from an online dating app. But I had picked him, we had texted, and I had no clue how he or I would be together in person. Nervous!

I think my ego really drove this pic. Here was a super successful guy (10 years older!) making a difference in the world in the ways I wanted to–helping people in developing countries get better access to capital, to help lift them out of poverty. I felt date pressure, I felt pressure to impress him professionally, and I just really really wanted it to work out. Part of me was probably confusing this awkwardly with a networking meet.

We met on a Monday night at a wine bar in Kreuzberg. I dressed nicely-ish, and judging by his body language I did a good job–he seemed to feel the need to impress me. About an hour into our chat, when I did exclaim to him that boy was I impressed, he breathed a sigh of relief– something that shouldn’t matter to me so much! Ok, time to chill Valentina! You’re doing fine see…

We stayed there from 8pm till after 11pm. All we had was 2 drinks that entire time. The talking was good. He did dominate most of it, but I found so many of his stories just plain fascinating, so it wasn’t terrible. He meandered a bit and never fully finished a story (my overly-categorical mind reacts by labeling this as ‘CEO behavior’, but not a big deal), but all the stories had so many interesting tangents. He seemed to travel even more than I have. We seemed to have equal passions for adventure and for making an impact in international development. These were all super, super great things. And we have other commonalities too: he was a software engineer for a long time; he is passionate about wine and travel; he’s an I/ENTJ, which is almost the same as me; he’s a leo like me; his birthday is just 4 days after mine.

Just halfway through our date, he was talking about his favorite park. and he invited me to go there with him next weekend. (I’m writing this days late, so as of now, that would be tomorrow!) At the time, I thought I was having a blast. I said yes! Later, I came home thrilled to see that I had “lasted” 3.5 hours on a first date without hating it, and that I had gotten a follow-up invite.

Clearly though, I see there’s something odd in how I phrased this. I felt more of an intellectual connection and accomplishment notch and feeling of approval, than a feeling of deep soulful connection with a peer. It reminds me of (many MANY) other times I admired an accomplished man in a professional setting and developed crush-like admiration for them. What little I’ve learned from this (the word “learned” is questionable, as I repeat the pattern a lot) is that there’s a tremendous difference between seeking approval from a father figure versus feeling compatible with a peer taking a partnership role. So I might be falling into that trap again. The other little red flag is I definitely felt inadequate compared to him and his achievements. (Impostor Syndrome, coupled with Women Syndrome?) Plus, he’s twice divorced, and has two nearly-grown kids. Much to dig into in a second date: to find out what phase he’s at, and what he’s looking for.

And so…. despite my reservations, I’m seeing him a second time. Because the other tendency I have is making too-quick judgments and not giving guys a second chance. As a new friend suggested over lunch this week, my feeling of inadequacy when presented by a more-successful man is not his fault, and shouldn’t be taken out on him! Or as my amazing Date #7 Sandy shared with me: accomplished men don’t tend to see women as competition; this distorted framing sits just with me.

The other great thing to learn from this: I always say I want someone smarter, more accomplished than me. How much of this is really true? Now that I’m presented with such opportunities, how am I reacting? Perhaps my reaction is an opportunity to grow and become less self-conscious; or, perhaps a fundamental compatibility will be more easily achieved by seeking someone of slightly lower stature.

(Read second date: #12)