Dating Advice: What NOT To Do On A 1st Date


Brad and Jen at the 2004 Cannes Film Festival before one Ms. Jolie entered the picture. Photo: Alan Davidson/WireImage

He was tall, handsome, well dressed and smelled great, everything you said he would be, Richard, and more, revealed the 32-year-old beautiful brunette Id matched with my newest client. The men and women always call me the morning after their first date its the highlight of my day.

I arrived 20 minutes late, she confessed, but I texted him to say I was still with a patient and would be there shortly. No worries, he wrote back, Ill order the wine. I was so ready for a glass of wine. This was looking good already. He stood as I approached. You look so beautiful, he said, and here I thought Richard was exaggerating.

It was the first time I had set up either of them. Matching couples on the first try isnt easy. Predicting chemistry is the hardest thing I do, but I spend a lot of time getting to know the men and women in our membership. I had a great feeling about these two.

The conversation flowed as easily as the wine, she went on. About an hour into the evening, we ordered dinner. He ordered for us. I just love that. He was kind to the waiter as well, asking for his suggestions, asking what I thought, making us laugh. I couldnt help but smile and wonder what our children might look like.

Right about now, Im saying, thats great, thats terrific, thats wonderful. I’m so proud of myself that Im ready to tap dance across my office. Looks like I was right, I thought. She continued.

By the time dessert arrived, I was planning the wedding. Then he asked, Why are you single? I replied that I had been in a three-year relationship that ended a year ago and needed some time to myself, but now I was ready to try again. ‘My ex and I are friends’, I said. He then asked if he could tell me about his ex. I said, ‘umm, if you want’.

Richard, I kid you not, he went on for 45 minutes in intricate detail about his ex and how horrible she is. It was painful to hear him say such awful things about someone he once loved. Finally, after hed dug himself into an abyss, he asked if he had said too much. I said no, but it was written all over my face. The spark was gone. I wont be seeing him again.

Romantic suicide isnt unique to men. Men and women both perform this ritual. But why? Everyone knows there are three sides to any story: his, hers and the truth. If you try to convince someone that you were right and the ex was wrong, you risk appearing bitter, narrow minded and emotionally unavailable. Who wants any of that in a lover? No one. So dont go there. Not on a first date. Not on a fifth date. Never.

Whether it was the romance of the century or a living nightmare, its over, so get over it. Try to live in the present, always looking forward. Never volunteer information about past relationships, but if someone asks, keep it simple: We are good friends which is probably all we ever were, or We were never meant to be. Then gracefully change the subject to something lovely about the two of you.

As for the client in the above story, his mistake was entirely my fault. Like actor Will Smiths character in the movie Hitch, its my job to coach the men on whatever they need most. I somehow missed that one. Damn!

Richard Easton is NYCs premier personal matchmaker. For more information on how to submit yourself for consideration into the club, please visit his site.