First up was Anna (I couldn't find a picture that looked like her). The date was made for a Tuesday night (originally it was for Monday but got pushed back a few days before the date). We were scheduled to go to a restaurant to which I’d never been. As usual, I arrived first.We were supposed to meet at 6:30 and by 6:35 I was wondering if I was going to get stood up for the first time. Just about that time the Manager waltzed by and told me that my date called and had hit some traffic so she was going to be late. About 10 minutes later she arrived.
She’s cute, sweet, has a nice laugh and a great smile. We get into conversation easily. I order ‘real’ food, she orders just an appetizer. She has traveled quite a bit and asks about my travel habits. I’m fairly stationary.
There’s a tool I’ve devised that has helped me figure out if the date is going well or not. If she’s not asking questions or furthering the conversation, it’s not going well. If she’s talking about something that happened on her vacation and it doesn’t have anything to do with anything, it’s a good bet that she’s not going to want to continue seeing you.
Most of the women are pleasant about it and can carry on knowing that it’s not going to work out. Some of the more assertive of them will cut things short by saying “you ready to go?” That’s the signal.
Anna went above that. When we walked out of the restaurant I asked, “So, is this something you’d want to do again?” and she said ‘Yes’. She then took my number and told me she’d call me but I really doubt she will. I, of course, stood there like a goon and didn’t get her number. I need to work on that.
Before I had even gone on the date with Anna (who was my 16th date, by my count) they set me up on a date with Sharon. She couldn’t meet after work so we’d have to do lunch.
I was led to the table where Sharon was already seated and we shook hands. Usually there’s a ‘settling in’ period but she began with the questions right away. First thing I notice as she’s talking is: she’s got a thicker mustache than I do. I know this is a problem for some women but most of them take care of the problem before they go on a date.She’s very outdoor-sey and into extreme sports. She drove a motorcycle to the date. I’m getting the feeling that she is more a man than I am. Either that or she is a latent lesbian… I can’t figure out which. She reminds me of a younger version of one of my aunts and I can’t get that image out of my head.
Somehow we get to talking about the dating service. I lament the fact that there is no feedback given to help me improve my dating practices. She purchased the “as many dates as you can in three months” which, in her case, turned out to be 3 dates – one a month. She is not happy about this.
She then proceeds to help me with my feedback problem by launching into her thoughts about me. “You’re a nice looking man,” she says “but too thin. I’m used to dating men that are much bigger than you. You have a nice smile and – thank god – a brain in your head. As far as I can tell you’ve got a good sense of humor”. This is all good right? Then why am I focusing on the things she’d change about me?
Then she wants me to reciprocate. At some point in my sentence I used the word “aggressive”. She thinks that’s too harsh a word and I have to agree, so we decide to change the word to “assertive”. She seems happier about that. She thinks it would be fun for us to hang out again but I disagree (I still feel badly about how it all played out but not with the result). She seemed okay with it and we soon parted company.
The biggest problem I had was with the timing. I don’t think I’m going to be able to do lunch again unless it’s within walking distance of my office. I left at 11:45 for a noon meeting. I made it on time – that was okay. But she kept talking and talking and I didn’t leave the restaurant until 1:00. I slunk back into the office around 1:20, hoping nobody noticed that I was gone that long. Luckily, no one missed me but I felt very bad about doing that.
So, no more lunch dates.