Strange First Date

It was a really odd first (and only) meeting.

I’ll call the guy Jack (name changed to protect the not-so-innocent and all that). When Jack first sent me an email from, I dithered about it for two days before I decided to respond. In all his pictures he seemed kind of nerdy, except one, where he was a cool dude perched on a stool. His profile depicted a warm family man looking for a permanent relationship.

Okay, so I was so bored one night and emailed him back. His following emails were chatty, full of info about himself and his close extended family. Phone calls were the same, with him commiserating with me about my concerns about my grandson. He’s a local businessman, easy to Google and verify, so I felt comfortable enough to accept when Jack invited me to dinner at a nice local restaurant, one of his favorites. I looked forward to meeting him and even went out and bought a new blouse.

Jack was waiting for me in the bar, with a drink he had just ordered. He was fairly nice looking and in good physical shape, although he didn’t appeal to me in the least. He greeted me pleasantly, I ordered a drink, then we were taken to our table. At that point things went downhill. All my attempts at small talk were rebuffed:

What’s good here? Everything.

Anything special you recommend? No.

How do they cook their fish? Any way you want. red flag!


We ordered, drank, sort of chatted. When Jack did respond, his eyes never met mine, red flag! always slid away to the left. That was the exit direction from the booth – did he want to escape? Did he find me hideous?

I pondered all his jewelry: two ginormous gold and diamond rings, a somewhat delicate gold bracelet, along with a watch (which I doubt was a Timex). Another red flag: red flag! a guy who wears more jewelry than you.

He commented that he never got hangovers anymore; when I asked how he prevented that, he said, “Drink more.” red flag! Hmmm.

Dinner arrived, and Jack dove into it like someone who was near starvation. We ate in silence.

After dinner, on our second round of drinks (I needed that gin and tonic at that point), we actually did talk a bit, and his eyes met mine once, for a nanosecond.

The waiter came by to take the check and got barked at. red flag! Uh oh.

Jack abruptly decided we should leave. We walked outside, and admired each other’s sports cars. Apparently that was enough build up or foreplay or whatever for him, because then he asked me to come to his place for a “drink.” red flag! I politely declined, Jack said we’d talk soon, and we both left.

The entire ordeal lasted 90 minutes. Thankfully I never heard back from him.smile_confused

Written by dazzled
  • Digg
  • StumbleUpon
  • Reddit
  • Twitter
  • RSS

3 Responses to “Strange First Date”

  1. Mandi says:

    At least you got a good meal. I’ve got a few stories I’ll have to share. It really makes you wonder sometimes!

  2. says:

    Strange First Date from…

    First dates from an online dating site can be unsettling, but this one was downright strange, with plenty of red flags….

  3. Kay says:

    Good point Mandi – it was a great meal!

Leave a Reply

CommentLuv badge
Back to Top