I recently had a date where, in the first 20 minutes, started wishing I was at home, watching the Bachelorette-and watching another two people on a date.

I met this man on an online app. He had a lot of nice qualifications and seemed interesting enough. And I had given up an opportunity to spend time with my euphoric crush because I don’t break dates. Big mistake.

Inventor-creative spirit-businessman-professor. All sounds good, right?


My first line was “I’m so excited to meet you. You have accomplished so much and you seem like such an interesting man. Can you tell me how all this happened and when you knew you had these gifts?”

Wrong opening line, but by past experience, this is a really good opening line. It shows I’ve taken the interest to investigate what he does, and am expressing interest, sandwiched in-between compliments.

What happened after that-besides my head spinning and leading to exploding was basically a close to two-hour lecture about the product development cycle-how the value of great design is arbitrary, and how the concept of in-line change is mandatory. Sexy, huh? And what a great opportunity to show someone how emotionally available you are.

Truly, my head almost exploded. I felt my eyes circling inside my head-unable to hear another word because I was on information overload. And in this two-hour time, I was asked one question, which was “What did you do today?”

So, guys who are reading this article, please let me give you some advice:

  • Ask as many questions of the woman as she does from you.
  • Show interest. A date isn’t an opportunity for you to show someone how much you know. (keep in mind, while dating IS like a job interview, you don’t discuss your day to day operations, PLEASE!)
  • If you hit a lull in the conversation, an ice breaker is to ask about a recent vacation or where someone would one day dream of going.
  • A date isn’t a sales pitch. Don’t try to sell yourself or your skills to someone. You don’t like being sold-don’t sell yourself.
  • Listen. Look someone in the eye. And if you know right from the start it won’t work, it’s okay to cut it short. No need to make this more unpleasant than it already is.

Remember, dating is a numbers game. The more you date, the more you’ll be relaxed and not pressured. And again, remember, we have two ears and one mouth. That means we need to listen 2x as much as we speak on dates-at least I was told this by a former boss who announced this in front of 15 people.

Lori Mendelsohn is a professional matchmaker. With a knack for introducing people who wind up saying, “I do,” she can be reached at smartfunnysingle@outlook.com. Her website is www.smartfunnysingle.com

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