A Tale of Two Italians

I slump over and sigh when I think of the idea of typing up my recent dating adventures, it's true. But I continue to remind myself that my (mis)adventures are to someone's great, great entertainment in the cyberworld. Without further ado I'll entertain you with my latest and greatest.

Date #1 (Wednesday) was with a guy who sounded promising on paper- a mix of my people and Italians (I figure when you add Italian genes to anything it can only be good!).

When I first got matched with him I almost deleted just on the basis of his name, which is an old man name, the equivalent of "Stanley" or "Melvin" or "Milton". Our emails were brief and text banter was funny, example: I had texted that he was "confirmed" for Wednesday night and he responded with a confirmation code.

So, fast forward to the date. Upon walking in, it was immediately clear to me that he was slightly cuter than his pics, more... "petite" somehow than he had appeared in two dimensions. Luckily I knew that lots of guys lie about their height in general, so I didn't wear my big clonker platforms and went with more conservative heels. But that always throws me off. Once a guy said he was something like 5'6 and I wore my clunkers and I spent all afternoon looking at the top of his head while we walked through the museum. I'm not saying don't be short, I'm just saying 1) give me a heads up and 2) I'd have to really, really like you to put my future kids through that genetic sandtrap.

I will now share with you the pro/con list I have made for the entertainment of my friends about said date.

*self-motivated, successful, friendly
*thoughtful (suggested we meet for Chicago style pizza when he heard I was from there)
*multicultured (half Persian, half Italian)
*likes to travel (!)
*polite (!!)

*bottom braces. Ironically, these were not the problem (I realize beggars can't be choosers) until at the end of the meal, when he announced "I have bottom braces, so sorry if there's a garage sale in them". (gagging as i type)

*said Chicago pizzeria was chosen because it's across the street from his house. he has a tab there

*when i commented on his unusual bicultural background and said there must be a fun story to his parents' meeting, he answered that his mom had died when he was 9 and so he didn't know. Um, there are a LOT of reasons you don't have to know, but tossing that out as your reply 40 min into the date is just awkward. Naturally I tried to steer the conversation to something less probing. Silly me. I asked if he had siblings (which, can we agree, is a VERY fair first date question) and he said "I was afraid you were going to ask that..."

Talk about down on his luck: "my sister died too. Of an overdose..." I know right now you're thinking I'm a monster, the Barbara Walters of the dating world, cornering her innocent interviewee until they burst into tears. But rest assured that promptly the phrase "In a lot of ways it was was a relief" was used in reference to said sibling passing. Also said: "When someone dies, you just go 'Ok, they're dead, moving on." Um. Someone call Dr. Phil.

CONs, continued:
*repeatedly commented on the fact that I was his first eH date. fine. but standing on the streetcorner repeatedly saying "YOU POPPED MY EHARMONY CHERRY! POP!" is not ok.

*recent travel = Dubai. Which was fine until I asked him what he liked about it and he said "The women were really pretty, with just their eyes showing. It was cool" When i pointed out that it probably wasn't fun for the women and that, as a women, wearing a burka might be, I dunno, disturbing, he was genuinely surprised, and sat back taking in my counterpoint. UM YEAH.

*politesse involved insisting he walk me to my car and repeatedly saying "Don't worry, i won't try to suck face with you". Did i mention he was 36?

Saturday I tried to bounce back with Date #2. Now, Patti, the Millionaire Matchmaker, is quick to warn that coffee dates aren't dates - "they're auditions". But I thought it was fine; the guy was native Italian, so maybe that's just how Italians roll! When with Romans, etc., right?

My date showed up and looked much like his photos, albeit something inside me kept saying "Jay Leno, Jay Leno" to me, which I wasn't happy about. He smiled a lot and had very pretty eyes, and I'd like to send a shout out to the waitress (thanks a lot tramp!) who stopped by our table to lean over and compliment him on them. We got into a talk about art licensing and he asked how I knew so much about it/how I got into licensing and of course found out I was a lawyer, at which point I felt interest wane a little, but realize that may just be my sensitivity to the fact that how attracted a guy is to me is inversely proportionate to how much he knows about my education.

He was very friendly but after a while I noticed he was not into asking me about myself AT ALL. We talked about his art hobby and his job for the most part. If you quizzed Mr. #2 about me, I think he could tell you that I like sitting in the chair facing the sun and that I have black hair.

That said, I like learning about people and I was interested to hear what he had to say. He did ask me about my sister's art. Like, a lot. The optimist in me says "this is a guy who is family oriented!" the realist in me says "this is a guy who wants suggestions on how to sell his art successfully!"

So the truth is I didn't meet my future husband tonight, but look Ma, I'm trying! And about Date #2 I'll leave with these parting words of wisdom: "Hint: heterosexual male looking to make positive impression on female hereby advised against Cirque du Soleil tee shirt"