The 40

Codename: “The 40”/ Firefighter

Location: Oliva in Sherman Oaks/Pita Kitchen

Website: PlentyofFish.com

There is always the curiosity of dating an older man. Could they teach me things? Are they better men? Are they more mature?

The answer: Yes and No.

So one day I receive an e-mail from The 40, asking if I would be opposed to dating someone that much older. He had no kids, was never married and certainly did not look 40 at all. Thus, the e-mailing began. Of course, these were the e-mails of conversation, the e-mails of friendship and mild flirtation but because he was out of town visiting his family, we could not meet.

As a red flag, I already knew, there was too much e-mailing already invested. Better to keep it to a few, have a phone conversation and get to the first meeting… otherwise you build it up.

This is exactly what The 40 did.

The phone conversation, while his voice was pleasantly male, gave me indication that perhaps, he was overly formal and dare I say it… he might be kind of… boring.

But he seemed like a nice guy, like a gentleman and despite my protests, he wanted to do dinner.

This is why I never do dinner on a first online date and unless I meet the guy first, I will not agree to it again, because this is the third time my concerns came to fruition:

I was dressed in a black dress, like a female appropriate for a sexy dinner. And while he was waiting for me in the back of the restaurant, while he was attractive, the second he opened his mouth, I just knew… no.

I had already warned him the possibility of this and he was already aware of what could happen on both sides.

I felt overdressed but I came to represent.

He was a good conversationalist, but was very business dinner. I thought this was a date not a meeting.

We ended up just talking about work. We talked very little of family, but in the end… there was nothing there, nothing he could convince me was worth pursuing further.

Then the check came, I threw in my credit card with his, and he let me.

Now here’s the thing, we had talks about the appropriateness of paying and he boasted that he always treated (even if I would have offered or wouldn’t allow it) and how generous he was with people. And he again was this contradiction even though it was his idea to do dinner and he essentially invited me. The first date is a very telling indication of a man and the fact that he allowed me to pay without a fight. Even if things don’t work out sometimes it’s better to be the better man.

Such was the case with Firefighter. A week ago I met a guy that worked downtown and had done Public Relations in the service and was now a firefighter who suggested we go to Pita Kitchen. I offered to pay and he refused it and paid, even though I could tell we weren’t quite going to make it to the next date. Firefighter had class even at age 30.

The 40 had fake class.