Be Cool, Don't Be All Like Uncool!

Many of my clients are single so inevitably, we share our dating war stories when we see each other. As a result, I have many scouts out there looking for a good guy for me and vice versa.

My one client called and said she was out in San Francisco for a family party and ended up meeting a guy she thought would be perfect for me. However, he lives in Ohio. I said, no problem, I have to go to Ohio for work all the time, I am happy for the introduction.

The next day I receive a friend request from him on Facebook. From what I could gather, looked like he was divorced with one kid. And, super cute.

Every time I would go to Ohio, I would reach out to him to see if he had time to meet up. Each time he said he had his son or a work commitment, so it never worked out.

Fast forward to 4 years later, I was out in Ohio once again and hanging at my client’s pool for the afternoon. This time I hadn’t reached out to him, so I told my client the story. She said, OMG, you have to send him a note and see where he lives, etc. We can meet him out tonight!

I thought, sure, I will send him a note, he will never be able to meet up anyway because he hasn’t every single time I have asked.

Guess what? He was available that night and was only a couple of miles from us. We continue to have drinks at the pool party, and I told him we would let him know where we ended up.

Well, I started to see a challenge occurring. The group of girls I was with was drinking quite a bit. I started to wonder if this was such a good night for a first meeting?

I told him we were thinking of going to this certain Country Club for dinner but still unsure. As the night progressed and the group I was with was having more and more drinks, I told him I didn’t think tonight was the best night to meet.

While we were at the Country Club, I only knew my client, all other people I had just met. They started talking really loud about a guy’s anatomy (in general). I was shrinking in the booth. All couples out for dinner around us kept looking at us like we should quiet down. Which, they weren’t wrong.

About an hour into my dinner, I look up and there is my potential set up standing in front of our table. GASP!

Now, this is where I made a fatal error. I should have said to him, let’s go to the bar and have a drink. Instead, all of the drunk girls told him to sit down and started drilling him with questions. And, they were very embarrassing and personal questions.

Especially for a guy we don’t know. It was like he walked into a lion’s den.

The look in his eyes was pure horror. Only second to mine. We tried to make small talk. but the girls kept interrupting to ask more questions.

After about one beer, he said, I think I am going to go. (shocking, not). We all said we are going to go too. As we are walking out, the girls yell – are you going to kiss her? I mean, isn’t that what you do on a first date?

Ugh, since I barely knew him, it was such a tough first impression, nothing that could or should be recovered from.

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Lesson learned? Don’t ever invite a guy into a group scenario if you are unsure of the wing women. If you do, separate him from the pack to have a chance of getting to know him!