11/01/2013 03:45 pm ET Updated Feb 02, 2016

'Maybe This Time...'

"Maybe this time...," sang Sally Bowles in Cabaret.

Yep, I'm a hopeless romantic, or should that be "hopeful romantic"? Am I brave? Am I being foolish? Being who I am, is this simply my path?

A number of years ago, a friend recounted the experience of being at a dinner party on the Upper East Side where, after coffee, someone posed a question to the assembled group of 10 men and women: "If you were offered a fantastic affair that had every quality you seek, but you knew it would end in a year, would you embark upon it?" My friend said that she was the only one who said yes. "That's why I belong downtown," she quipped.

"A whole year! Wow!" was my response as a man who was just beginning to believe that I might live for more than a few years. In certain ways I'm still operating with that "live for now, because there may be no future" attitude. It brings vitality, but is it also limiting the space for timely consideration? I do not regret my willingness to take risks with my heart. However, slowing down might open up new horizons.

In life we are often holding opposites. Just as I feel a tension between ambition and ease, I feel a tension between a more traditional relationship based on the plan to stay together indefinitely and being single.

Since ongoing, deeply committed friendships with my exes is my norm, it's not that hard to imagine my next boyfriend or myself moving on from the partner form at some point. The connection that brought us together can be nurtured in a new context. As my friend Felicity Mason always said, when it comes to relationships, "I don't subtract; I only add."

Recently I met a fellow. He's about to turn 30, of mixed race, French, a music promoter and just so curious and engaging and sweet and sexy. Logic says, "Run the other way!" but my heart says, "Take a chance! You'll give and get and see." My heart usually wins, but this time, I'm going to step back. I'm not going to take the chance. The drama of youth isn't attracting me. Recognizing that a person needs to grow up before they could be suitable for me feels mature. I have met other guys in the same age group who are more or less together. I want someone who can be there for me at times.

Most of us are testing potential new boyfriends/girlfriends, although it may not be conscious. Do they ever pay for a dinner or bring me a flower? Do they offer me solace or give me insight? Can we switch roles? I need to both give and receive with a partner.

Ultimately, it comes back to the best advice a therapist ever gave me about dating: Put aside the list of the significant other's attributes (funny, smart, handsome, accomplished...), and ask yourself the critical question: "How do I feel about myself when I'm with him?" If you feel good about yourself, continue. If you feel inadequate or nervous or insecure, leave tire tracks. In the first years of my relationship with my most recent ex, I wanted to be the person I saw reflected back to me in his eyes. I felt smart, funny, kind, interesting and interested. "Hang around!" I told myself. I'm glad I did! We had several amazing years, and another couple of years with struggles where we both grew and learned. Our separation was part of a successful relationship that continues. Love was not the issue. The inability to accommodate each other's limitations is what pulled us apart. We are better as intimate friends.

Romance and love are wonderful. I can handle disappointment. I want to be in the game of life. Therefore I remain open... and If I knew I'd only have a year of bliss and then would have to let go of the form, I'd continue. If I knew I'd have five or 10 years, I'd feel like I'd won yet another lottery!