I’m No Boy Scout

The first time I proposed to a girl was via email.

Shockingly, she said no.

I suppose I should provide a little more detail. This all happened several years ago, when I was youngish, had a much fuller head of hair, and still sported the goatee. I met the girl in question, whom we will call Pomona, on a free trip to the Caymans, courtesy of the Pretty Boy. I know you’re probably thinking that I was a fool to let an island encounter get me carried away and lead to a marriage proposal. OK, there’s a large percentage of you who don’t believe there was an island encounter in the first place, and, sadly, you are quite correct. Many of us on the free trip hung out and partied on and in the white sand and blue, blue water of the Caymans, and it was a magical week. But not quite so magical as to lead to a semi-random hook up for me.

Nonetheless, a number of fun people from that early December trip – most of whom lived in the Philly area – decided to try to have some more good times together by coming to D.C. to ring in the new year with those of us who were clever enough to already live in the D.C. area (i.e. me). Many emails flew around (this was before IM really caught on), and I traded several with Pomona. In one exchange she divulged 3 highly unusual things:

1. She and her dad had season tickets to Temple basketball games, not because they had any connection to the university at all, but solely because it allowed them to see some college hoops in person.
2. She happened to know off hand that UNC had lost the night before, but was bummed that she was unable to watch the game.
3. She liked Bobby Knight. (As a speaker. Mainly, anyway. She was trying to book him as a speaker for some event she was coordinating. I point this out not because that makes her right or smart but it’s such an unusual stance for anyone other than an old school IU fan to have.)

That was quite a lot to take in all at once, and I couldn’t help but be more than a tad shell shocked. I decided to go with some email flirtation, and I concluded my response with this gem:

I have to admit that I am fairly disturbed by many of your comments.  A woman who likes college basketball?  What?  She pays close enough attention to know that UNC lost last night?  She likes Bobby Knight?!!  It's a crazy thing.  I can't really explain how the existence of these things turns my world on its ear.  This may sound a little forward . . .  I mean, I know I don't know you that well . . .  but, um . . . well . . .  will you marry me?

Those of you who know about these things will know that my efforts at flirtation are doomed to fail because, as a middle reliever, I’m actually incapable of flirting. And, seriously, that could have possibly been just scary enough to scuttle the whole New Year’s Eve outing. However, my email wasn’t really about marriage. It really just meant, “I’m impressed by you, and I’d really like to date, or at least shag, you, and I’m going to attempt to convey that desire in a possibly creepy and definitely opaque manner that I misconstrued as charming, funny, and flirtatious.” As it turned out, Pomona wasn’t outwardly creeped out (or she at least hid it well), given this response:

I'll have to say no to the marriage proposal today...though, if you present me with a really big ring tomorrow night, I might reconsider.

That was actually somewhat funny and definitely cleverly deflecting of the whole issue. I suppose it could be summed up as, “I’m not particularly interested in shagging you, but I see no reason not to keep my options open for the time being.” Of course, I took it at the time, as was my wont, to mean, “I’d get wit cha if you were rich.” (I believe Kanye had a song about that sort of thing.)

I wrote something back, inevitably about how tough it was on an Abs in those days, and let the whole thing drop.

Right?

Wrong! At least about letting it drop. Yadambetcha I wrote about how tough it was on an Abs in those days. Because it was. However, instead of letting it drop, I opted to respond in a clever, charming, and witty way, even if doing so made me risk going a bit over the top. I decided to buy her that big ring and give it to her the next night.

So, when we met up at the hotel where we were crashing to head out for the New Year’s Eve festivities, Pomona surprised me by immediately asking, “Did you get me a big ring?” I wasn’t expecting her to continue our little joke, especially in front of our whole group of people, and I was more than a little perturbed by her stealing my surprising and charming move’s thunder. Still, there was nothing for it, so I somewhat reluctantly reached into my pocket and handed her a big, red ring pop. I suppose if I were being especially clever, I would have gotten down on a knee or something, but I was too put off of my game. She said, “Thanks,” smiled and we all headed out for the night.

An hour or so later, Pomona had a brief moment to chat, and, as she looked at the big sucker on her finger, I asked her about it: “So you were expecting me to give you a ring pop?”

“Yep.”

“Really?”

“Well, it was the obvious response.”

Sensing my distress at the utter failure of my charm, at being so “obvious,” she opted to be nice: “I liked it though. It was still funny. I would have liked it better if it was a green one, though.”

She was borderline stunned when I reached in my pocket and pulled out a green ring pop. I hadn’t been able to decide between the red or the green, so, big spender that I am, I bought both. “I definitely didn’t expect that,” she told me.

It was dumb luck that I was prepared for that situation, and one might think it was looking good for the Kid right there. What happened next, you wonder? Did Abs shock the world and manage to ring in the New Year with some fireworks? Did he capitalize on this unprecedented show of suavity?

Absolutely not. The details are a bit fuzzy, but at that point, some of our friends came over with shots, I proceeded to get famously drunk, and she went home with one of the guys she had traveled down from Philly with, which was really her plan all along, unbeknownst to me.

So what’s the point of this, you ask? I’m not exactly sure, other than that I was recently thinking about this story and how that second sucker ring made me so prepared. And it just didn’t matter because she just wasn’t particularly interested.

The next time around, I wasn’t nearly as prepared. I only got one ring for the Girl. Lucky for me, she didn’t say she would have preferred a green one; she just said, “Yes.”

So let those boy scouts “be prepared.” Maybe sometimes it’s better to just get it right.