Even getting the girl drunk won't help you

They say the best things are worth waiting for.

I could share many, many amusing things said by Tommy, the guy I went out with last night, but I’ll just skip to the gold nugget I received at the end, while standing beside my car:

“So, not to be awkward or anything, but, why do I get the feeling that if I leaned in to kiss you right now, you’d push me away?”

Not to be awkward, indeed. What could I tell him?

“Because your fondness for dancing makes me question your masculinity.”

“Because you insist on familiarizing me with famous bands (like the Black Crowes and the Gorillaz) that I already know, continually insulting my intelligence.”

“Because you think that telling me, ‘You don’t wear a lot of make-up like some girls,’ is a compliment.”

“Because earlier tonight, you pointed out the fact that I was checking out another guy, making our time together even more awkward.”

No, despite my beer buzz, I didn’t have the heart to use any of these reasons, so I took the high road and went with,

“Yeah, I probably would push you away. I’m just not attracted to you.”

But that wasn’t enough for Tommy. He wanted to dig himself a deeper hole.

“Well, ok, ok,” he stammered. “Is it the age difference, do you think?”

Tommy is 29 – eight years my senior. But let me assure you, his age wouldn’t be a problem if he were good-looking. Again, he asked for the truth, and he got some version of it.

“No, not really,” (I was grinning. You might think I'd feel sorry for him, but this was too funny.) “You’re just not my type.”

This turned out to be exactly what he was hoping NOT to hear, but I couldn’t feel bad when he was asking for it. With that, we went our separate ways and the date was over – I, marching off victoriously relishing my free drinks, and he, slinking off without the goodnight kiss he’d been waiting for.

For all the Tommy’s out there, I offer this advice:

If, at the end of the night, you have to ask a girl whether or not she’d kiss you, then she probably won’t. Even without your glasses, I’m pretty sure you’d see the signs if she wanted you…or wanted to run away.

Better luck next time.

The death of a date

So my date with the lawyer – we’ll call him “J” – went pretty well last night.

He turned out to be a nice guy who made a handful of fatal errors during the night. The date was dead.

But to be fair, J had a rough time of it in the first place, since I’m convinced the NYPD officer I'm seeing is the best thing to happen since sliced bread.

However, in your own interest, I’ve broken down the mistakes J made so you’ll know what to look for in a date that is not gonna work out … and then run away!

1. Inviting a random guy friend along.

This should have been my first blaring siren.
J told me over the phone before we met, “Oh, my friend has nothing to do so he might tag along.”

I think he ditched the idea after I made it clear that I was unimpressed, but what was he thinking? How awkward to have to impress both him and his friend! On top of that, it makes him look like he doesn’t have the balls to spend an evening alone with me.

2. Asking if yall can take your car.

His perfectly good car is sitting right there by yours. He shouldn’t ask you to drive him – he shouldn’t even want to. I know guys who feel foolish in the passenger seat and they’ll only let me drive over their dead bodies. But on a first date??

This one is especially true in my case, since I had already driven nearly 30 minutes to meet him at his place.

3. Ordering your meal for you.

This was J’s doing-in point.

I think most guys know this one – I never thought it would actually happen to me.

J and I decided – no, actually, he decided this too – that we’d split a rack of ribs at the barbeque place we were at.

When the waitress told us it came with two sides, he ordered both without even looking to me for my input!! Even the waitress looked at me, surprised by what had just happened.

4. Flirting with the waitress at dinner.

I didn’t care by this point. I knew I was far from interested and I was getting a free meal, but it was icing on the cake.

5. Coming home after the date to play video games with a friend and inviting you to watch.

But, Caroline, you say, isn’t this guy a 24-year-old lawyer?

Yes, but lots of “men” look like men when they are actually just boys. Clearly, J didn’t want to get laid last night when he made this move. If a guy is going to play video games on a date, he can at least offer to let me play.

By this time, I’d have enjoyed kicking his ass at Mario Kart!

Blind date

Oh my God.

That was my first thought when I spotted him across the street, walking toward me. I knew it was him. There was no mistaking it, but I was still praying that I was wrong.

I had agreed to meet one of the men I met online Friday night, despite the fact that I already knew I wasn’t interested. I figured I’d at least make a friend and have someone fun to hang out with. Nothing, however, could have prepared me for this.

We chatted on AIM Thursday night and agreed that I would call him (I didn't want to give out my number) Friday to let him know whether I’d be free that night. We'd been talking online for about two weeks, and he had sent me a photograph a while back, so I knew he was Indian.

It didn’t bother me – I’ve been infatuated with men of many different ethnicities over the years, but I made the mistake of assuming he was like them. Americanized.

He wasn’t.

I knew it as soon as I called – I was answered by a very thick accent. Very.

He was fresh off the boat, all right. And that's not a bad thing...unless I'm hoping to be attracted to you.

But what could I do at that point? By the time I had registered the fact that I had to decipher his every word, I already heard myself telling him I was free that night.

So it was settled. I would meet him in the village for dinner at 7:45 p.m.

The time came and went. He was still on the road. I waited. He was still trying to get there – did I know where 258 was? This wasn’t happening.

It’s one thing to have to wait for a date you’re excited to go out with. It’s another to have to wait for one you’re dreading. On top of that, he couldn’t understand my directions, and I was getting irritating.

“Go down 110 and make a right on Main Street,” I instructed calmly.

“What?! Whoa – you want me to come to your place?”

“No! Take a right on Main. Main street!”

So this brings us to me, watching him cross the street, an hour and a half later. I saw him from a distance. He was like a lanky ape, with his mouth hanging open, lumbering toward me.

I’ll skip the brutal details of dinner, and get to the point.

Yes, he bought me dinner. He called he gorgeous. He opened the door for me. But it was awkward, and I found myself watching the clock (conveniently hung on the wall opposite me) and stretching for something to talk about.

The point is, don’t go out with someone you don’t like. That “free” meal you’ll console yourself with later? It’s not really free – you paid for it with the hard work you put into acting like you didn’t want to run away all night. It was also work trying to think of a reason to skip drinks and head home early.

In the future, I screen all dates by phone before making plans.