Lena and I met on Instagram. She was definitely my type. Russian, slender, creative, with eyes that burned through your soul, and, as a model, she had a flexible schedule. We both had just come out of recent relationships, yet, they were both solidly in the rearview mirror, so we were open to dating new people.

I’ve been happily divorced for over 10 years, have a great relationship with my ex, and incredible kids. Having experienced a lot when it comes to relationships, I know what I want in a partner and have come close twice to hitching up again but it hasn’t happened yet.

My last girlfriend was Hana. She was an amazing Russian woman, but baby pressure came too early for me and with an ultimatum. I don’t do well with that stuff. I LOVE kids and being a dad but they are a serious commitment. I’d have more children but it takes time for me to feel comfortable enough with someone to bring new life into the world.

Most first-time parents have no idea what they’re on the hook for. They romanticize about baby land but it’s not all baby powder and unicorns when the 2 a.m. leaky diapers come calling, and the lack of zzzz starts hitting.

With Lena, our first couple of dates were on Zoom, and I had to get creative, something I actually like doing. It always puzzles me at the lack of effort my fellow single guys put into dating. It is really not that hard to make small gestures like flowers, a nice card, or a Parisian candle.

I sent her dinner and a couple of nice bottles of vino from Flatiron Wines in Manhattan. I ordered the identical for myself. We ended up having a nice long conversation over dinner and sorted through the wine together.

It was actually an incredibly effective way to know someone and develop a deep connection before we’d meet in person a few weeks later.

Our first in-person date was a flight to the little-known Fischer Island, New York in my RV8 airplane. I brought lunch for us, some pasta that I had cooked the night before, made a salad, and packed it all up in my backpack — I love to cook.

Landing at Fischer in March of 2020 was surreal. The island was mostly deserted, as we parked the plane and walked to the beach where we had lunch and then went off to explore the island on foot. I remember how quiet it was. Some things I really enjoyed mid-pandemic was the quiet and that mother nature got a short much-needed break from us humans. I’ve often said COVID is to humans as humans are to planet earth.

We walked around half the island, sat under a big oak tree that overlooked the harbor, and had our first kiss. My pulse was racing because I really liked her. After dating over a hundred women in New York and abroad (I’ve been on a lot of bad dates!), I’ve gotten very selective. The upside of this is that I do know how to make a date special and I think a man’s first kiss with a woman should be memorable and not some sloppy midtown bar make-out session. So I leaned in and kissed her. It was incredible and a bit awkward all at once.

Departing the island, I circled to the east, did a low pass on “our tree,” and took a photo with my iPhone. Dating in the pandemic started out as a fairytale but would come to a tragic end for me.

Fast forward.

It was a really great connection but we had issues of distance.

I gave up my New York apartment, put my plane in the hangar, and went to Puerto Rico.

Lena loves horses and the beach: Puerto Rico has both, so I thought it would be an easy sell. However, the draw of New York was too strong for her, and like most relationships, issues started to surface. An abusive ex, a restraining order, and more.

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It was complicated, and trust started to erode. Especially after getting a DM from someone who claimed to be an ex of hers, saying that she had cheated. I shared the message with her and we talked through it. Although the message came when I thought we were in a solid place in our relationship, it nevertheless shook me. I was even designing a ring with my jeweler friend.

At this point is where my own bullshit also started getting in the way. I don’t have too many bad habits, outside of obsessing over chess on Lichess.org (a great site!), watches, and looking at airplanes online. But — and it a big but — I sometimes flirt with women on Instagram and social media when I start feeling like the relationship is eroding.

What I thought was a harmless defense mechanism was actually destroying the foundation of trust that I had worked so hard to build with Lena and I should have been more open about this.

She got really upset about this, and rightfully so. It was enough to break us apart, just when the ring I designed arrived in my New York mailbox.

The problem today is that there are too many choices. We are overwhelmed by dating apps and social media to the point that we trick ourselves into thinking we can easily find someone else around the corner, instead of investing time into what we have.

I can tell you from personal experience that nobody is perfect.

I’ve also tried the polyamorous stuff but it’s just not for me. I want a deep connection in a partner, and for me, when it comes to romance, sharing is not caring.

So I went back to work on myself. I did some therapy and watched a lot of Teal Swan in order to work on myself and my own bullshit.

It’s getting better for me but I still get distracted by dating apps. Maybe I’ll take a break for a while.

But I am making progress on important issues that will let me be a better partner in my future relationship. I also feel like I know a lot more about how to keep trust once it’s built. And, guys! Women want to feel safe and secure. This is all about trust and safety for women.

The truth is, there are a LOT of shit dating sites and advice out there.

Be careful who you talk to because most of our friends are not in great relationships and they are the first to dish out their expert advice on who we should and should not date.

I event took a trip to see my 90-year old grandmother in Canada and ask her advice. She was married to my grandfather for most of her life, they’d been through a lot. Now there’s a great resource.

I also look for people in healthy relationships that I admire and ask them for advice.

Additionally, there are great books like Attached, which talks about attachment theory. Incredibly insightful. There is also a lot of cultural bias we walk around with and it’s important to realize that about yourself and a potential partner.

Recently I was on Clubhouse in a standing-room-only virtual talk on dating and was shocked at what I heard this “dating coach” tell women.

She was advocating lying about their age to a room full of thousands of women — and a few men like me lurking.

I was horrified. I should write an article for Men’s Journal about this.

How could this person be so damaging?

Trust is the key in any relationship and starting off by telling lies is a sure way to plant cancer in a relationship. And this tumor will grow over time and become fatal.

I was horrified listening to this.

Maybe I should write a book for women on what good men look for in a mate because this gal had it all wrong.

Now what?

I’m trying to meet women naturally, rather than through dating apps.

I have a shortlist but I do know what type of person I am attracted to. I generally prefer Russian and Ukrainian women, to be honest.

Before you roll your eyes, and hear Man Eater, by Hall and Oates playing in the background, hear me out.

There are a couple of reasons…

Maybe I watched too much James Bond as a kid but I actually like the Ukrainian and Russian accents, I find them sexy. They always take care of themselves, and even in a relationship, they don’t slack off. Nails, hair, self-care, diet, all of it. I also like their mentality when it comes to traditional relationships between men and women. A guy can be a guy…

Eastern European women can be feminine, and at the same time powerful and career-oriented.

They are very direct. That’s a gold star for me.

They do not trust easily, you have to earn it. They admire family (e.g. I don’t get penalized for having kids), and understand the differences between men and women.

I can actually be a man around them and be unafraid of it! This may sound strange but a lot of American women, many of whom I’ve met, seem lost and confused right now, especially when it comes to the identity between the sexes.

I’ve been scorned for being a gentleman in New York.

Ladies, there are a LOT of great guys who didn’t get to where they are Harvey Weinstein style.

What happened to good old-fashioned (also my favorite drink) chivalry and just being a gentleman?

Women can be powerful and feminine at the same time.

I was raised by a powerful independent mom (SBA businesswoman of the year. Go, mom!). My grandmother owned and ran a collection agency in the ’70s. She named it Brandon Tyler Webb and Associates to get around a woman-owned business in 1970s LA.

It’s ok to let us be the guy who changes a light bulb, fixes things around the house, takes care of the odd spider in the bathroom, and opens doors.

Some women I’ve encountered (and now learned to avoid), especially in New York, are combative about a man opening a door for them. If we’re labeling, which we are these days to at an alarming rate, I’ll flip it back to the Feminazis and call this “toxic femininity.”

So where does this leave me? I’ve let a lot of great ones slip away but it’s all been a learning experience for me. I now know a little more about me, and the things I need to do in order to keep a keeper.

My list of desired attributes in women isn’t crazy.

What am I looking for?

Kindness, self-awareness, a healthy lifestyle, a flexible schedule (I like to travel), and a beautiful inner-world. Also they have to be of child-rearing age (I date younger because I’d like the option of more kids)

That’s it.

I spent the last few months, after some self-work, calling some of my exes to apologize to them. I like to build bridges (not burn them), and thankfully most of them appreciated my apologies for things done in the past.

I have made a fresh start again, and it feels good.

Recently I met someone and the butterflies in my stomach feel good.

“What we seek is also seeking us,” said Rumi.

Love in the age of COVID is possible.


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