I decided to give J-Date a whirl. Oy.

There are lots of cute Jewish men looking for relationships, and my profile caught the eye of one man in particular. David was very cute. Originally from Los Angeles, he was a partner in a downtown law firm and a New York resident for the last twenty years. We had a very fun online chat, and he closed a date with me almost instantly.

We decided to meet at the fountain at Lincoln Center, and from there would go to PJ Clark’s for drinks and nibbly bits. When I spotted David, he was every bit as handsome as in his pictures. He fibbed about his height (definitely 5’6”, not 5’8”) but in all the physical package was quite good.

After being seated at a great table, David admitted that he took a look at 1FineD8.com (which is fine as I tell all my dates about this blog and it’s mission). That said, David proceeded to ask me a very interesting, yet inappropriate first date question…

“As a relationship expert, I’d love to get your take on my last two breakups, ok?”

As we all know- or should know- discussing past relationships on a first date is a major dating sin. The first date is about moving forward on a road that hopefully leads to a connection. It’s not meant to be a forum to perform an autopsy on relationships past.

“Well, David, a first date really isn’t meant to discuss past boyfriends,” I responded.

“Indulge me, handsome… just for a moment,” replied David, flashing his sparkly and very convincing smile.

I indulged, giving David his moment. His moment lasted 90 minutes. Here’s a brief synopsis of what came out when he backed up the dump truck and poured the contents of his failed romantic past all over my 1FineD8…

“I’ve had two relationships. My last relationship was an open relationship, and after two years he found someone better and dumped me. That really hurt, almost more so than my first relationship’s ending. My first and I were together for ten years- open relationship. I was in Cleveland a lot for work, and I developed a relationship with a man there, which lasted almost a year. Well… the Cleveland guy came to NYC and I introduced my partner to him (he knew all about him). Long story short, they really hit it off and now they’re together living in Cleveland.”

“Your partner dumped you for your boyfriend?” was the only response I could give.

“Yes. I was really surprised, but not surprised. It really hurt. Now I’m dating again and dating makes me anxious. I believe dating is just a shopping excursion for someone that is destined to disappoint me and eventually leave me for someone better.”

At this point, my wine glass was on its second fill and close to requiring a third. I decided to wrap ip this therapy session… I mean first date.

“Well, David, it seems the commonality between the two would be that your relationships were open. Maybe that is something you don’t want to repeat in your next go. Would you consider having a monogamous relationship?”

“No. I want to keep my options open.”

“In that case, it seems like your two Exs also kept their options open, and they chose to exercise their escape clause. They just beat you to it.”

“That’s true.”

“Maybe you need to meet the guy that going to make you want to seal the deal- the man that brings you so much joy, so much of a connection that you only want him. You say that you’re afraid that a potential partner will leave you for something better. Maybe if you focus on just one man and enjoy that process, it will bring out the best David possible. The David that he’s never ever going to want to leave.”

“That sounds like a lot of work, Craig.”

And with that, I asked for the check.

1Gr8Lesson
First dates are meant for two people to get to know each other. First dates paint a picture of how you communicate, how you laugh together and if there is a spark of chemistry that leads to a repeat performance. Bringing up past breakups casts a negative cloud over this initial meeting, in my opinion. The cardinal rule to follow when it comes to a first date is that all modes of transportation are in bounds for conversational topics, with the exception dump trucks and moving vans. Discussing your Ex is about as sexy as planning cohabitation before your waiter can even offer you a dessert menu.

On my date with David, I basically witnessed an autopsy of two failed relationships and was asked to give my opinion on the findings. It wasn’t the question of open vs. monogamous relationships that was a deal breaker for me (frankly it’s not really debatable because what works for some couples may not work for others and is really a decision to be made and judged by the two in the relationship) but the fact that I really didn’t get an opportunity to learn what made David tick. I didn’t get to see if we had anything in common, and there was certainly no opportunity to see if there was a spark. What I did learn, however, was that David was still stuck in the drivers’ seat of the dump truck containing his past romantic relationships. He was so not ready to move on to a new relationship. I was concerned to hear his negative views of dating as a portal to ultimate disappointment, and the major red flag was when he balked at the concept of working at a relationship.

Definitely not 1FineD8.