The Tale of Two Dates

I promise, this post will be shorter than a Dickens novel. But, not by much!

So, last week I went on two first dates. This is big for me. I don't think I've ever been on two first dates in one week because a) although I am fabulous, I'm not quite THAT fabulous and b) I'm one of those, I meet a guy-I fall for a guy-I forget that there are even other guys in the universe-all before the first kiss, kind of girls.

Or, I used to be that kind of girl. I'm working on it.

So, I think my shrink (aka dating coach) would be proud that I accepted two dates in one week. Date #2 I actually met first. My friend, K, and I met him at a dance. He's cute, despite the fact that he clearly has two left feet. And he's quiet. Like...super quiet. Like...he's one of those people who can stand in a corner alone in a room full of people and not even notice that he's alone.

In other words...this guy is nothing like me.

But, K dug him and since she's all coupled-up, she invited him to come dancing with the intention of throwing me at him. Well, it kinda worked. I finally talked to Mr. Bashful and it turns out that he has a rather dry, but funny sense of humor. We work in the same (not very big) industry. We went to the same college (me for undergrad, he for grad school.) We're the same age. We're both divorced. Yadda, yadda, yadda.

So, he asks me out. I say yes. I give him my number and wait for the phone call.

Monday morning I get an email from a guy on match. He thinks I'm cute. He likes my profile. He mentions enough of what's contained therein for me to know that he actually read the thing.

He wants to go out...like, now. None of this send an email, wait three days, send a reply, wait a week, ask for her number, wait three days, send a text message, wait a week, then promise to call.

It's just, "Hi. I like you. If you like me, let's get a drink tonight."

Refreshing.

I check out his profile. Pros: He's got a really cool arts-related career. (I like creative people.) He seems sincere. He seems serious (when it comes to relationships) but funny and optimistic (when it comes to life.) This is looking good.

Cons: His photo is artsy and kinda cool, but too far away to tell what he actually looks like. He has two kids already and isn't sure if he wants more. And he's a little older than I'd prefer (but I seem to be liking older lately, so I'm not sure how much of a problem that is.)

I say, sure. Let's go out, but not today.

Before I hear back, I get a call from Mr. Bashful. I give him the option of Wednesday or Friday. He picks Friday. We agree on Italian and he says he'll call for reservations.

So, when I do hear back from First Date #1, I tell him Wednesday's the day. He says cool, but he's got his kids til 8. This is perfect, I think. An after dinner drink is the ideal amount of time to spend with someone you've never met. If we don't hit to off, we're only stuck there for an hour...tops.

Wednesday comes around and I'm feeling a serious lack of excitement and anticipation. My brain has filled in all the parts of the photo I can't see and I'm convinced this guy looks like a mouse. Maybe a cute mouse? But, still...a mouse.

See? Mice can be cute. But I wouldn't want to date one!

By the time I get to the restaurant, I'm sure that I'm not going to be able to pick this guy out from the crowd. And, I'm right, because the guy who comes up to me and says hello is less like a mouse and more like Steve from Sex and the City!

I'm not sure this is a terribly literal comparison. If I were to put up the actual guy's picture, you might beg to differ. But, like Steve Brady here, I find Date #1 to be adorable.

So, long story short, my date (for the sake of simplicity we'll call him Steve) turns out to be a pretty cool guy. He's funny. Easy to talk to. Listens to what I say. Looks me in the eyes. Answers questions honestly and thoughtfully. And, I gotta say, he's a damm good kisser. All in all, a pretty fabulous first date!

But, remember, I'm still on the hook with First Date #2 with Mr. Bashful? So, Friday rolls around and I head out to the Italian part of town. He's waiting outside. I give him a hug. We go inside and the restaurant is about the size of a postage stamp...good thing he made a reservation! We get a little shelf (not even really a table) at the window and try to make small talk.

It's painful.

Me: How was your week?
Him: Good.
Me. Anything exciting happen?
Him: No.
Me. So, what did you do all week?
Him: Stuff.

This is trouble. Before too long, I resort to asking him what he watches on TV (sports) and what he likes to do on the weekends (running and biking.) I even ask him for the coolest travel destination he's ever been to (mine's Africa) and he says, "um, East Providence. And North...North Providence."

This is clearly a joke. It's also clear that he has no answer to my question.

On the plus side, the food is fabulous and the service is quick. So, within an hour and 15 minutes, we're back on the street.

We start walking. I have no idea where we're headed. I ask him. He points in a random direction. Eventually, that route takes us past a subway station and I say, "Oh is this where we were headed?" He says, "Not really." I say, "Okay, did you have something else in mind?"

Long, long pause.

Finally I say, "It's a beautiful night. Want to go for a walk?"

This is how we end up on a completely aimless walk around a deserted downtown with nothing much to say. It's not painful, but not enjoyable either. I keep thinking I might get him to loosen up and I might discover a hidden gem under than awkward exterior. Do you want to know what I found under the awkwardness?

More awkward.

(Side note: Have you ever noticed how awkward the word "awkward" is? My fingers never quite want to type it. My tongue trips over the two w's. I love it when words are what they mean, you know?)

Eventually our aimless walk takes us past another subway station and I make some excuse about needing to get up early on Saturday. I give him a hug, and scurry up the steps as fast as I can. Date over.

So...one week. Two first dates. One was great. The other was awkward. Two lessons learned.

1. I would rather have one great first date and one awful first date than two mediocre first dates.

2. There's a reason people date more than one person at a time. I've since gone on a second date with the-man-we'll-call-Steve and it was very nice, but we still have a lot to learn about each other. If I hadn't been distracted by my Friday date, I might have already started planning our wedding in my head. (Don't laugh. I've done it before.)

So, now what? I had a phone "date" with an eHarmony guy last night. He just texted me. He wants to go out this week, but I just don't think I'm into him. Here's the problem:

Pros: He's cute. Nice. Funny. Friendly. Social. Owns his own businesses (okay, they're a couple of Dunkin Donuts, but still...shows initiative.) He wants kids and he's clearly serious about finding someone.

Cons: He has a wicked strong Boston accent.

Part of me thinks that I should go out with him. First, he'll keep me from going gaga over pseudo-Steve. Secondly, who knows...maybe I'll like him!

Thoughts?