How to Make Good Friends Out of Bad Dates

I'M ON AN (IMPROMPTU) VACATION WITH MY BEST MALE FRIEND!

Yes! On an island off the coast of the beautiful American Northeast. A cottage fell into my lap on Monday night: A pregnant friend of mine rented the place with her husband and was driving up to spend a couple weeks here when she started feeling strange. She and her dude promptly turned their car around to make an emergency trip to her doctor — and my friend is now spending the final three months of her pregnancy on bed rest. My buddy is one of the most upbeat little ladies I know, and she's handling the whole thing like a champ ...

My writer friend Teddy was with me when I got the text from my pregnant pal about the suddenly free cottage — and I was about to turn down her offer to make use of the place when Teddy convinced me I should take a little working holiday ... and that I should take him along! He'd come along for the long car trip, read me the directions while I drove, and protect me from wolves (or at least sea pigeons). It began to seem like a very appealing idea. And since both Teddy and I can work from more or less anywhere, we decided to go for it.

I've already almost burned the house down — who puts decorative covers on an electric stove top? — and I forgot my bathing suit. But other than that, we're having a fine time. We laughed the whole way up, psychoanalyzed each other a little last night, and are getting ready to take a stroll on the beach.

But first! I must post!

On Tuesday, preparing to get the hell out of Dodge for a while, I started taking care of business: running a few urgent errands, tying up loose ends. As I was going through my mental to-do list, it occurred to me there was a certain personal-life box I needed to check off: I wanted to become friends with the God-Believer. As you may recall, he's a guy I went on a date with a while back. Although I didn't feel the elusive spark with him, I did really enjoy his company (the whole God thing aside). He was very smart and quite interesting. He's also doing cool things, professionally.

I wanted to be friends with him, but I wasn't sure how to navigate that terrain.

In the past, when I've gone on dates with guys who were great in all respects except that I didn't want to unbutton their shirts, I often found myself in the position of power: The man would ask me on a second date; I'd say no, as nicely as possible (here's how to do it); and if I truly wanted to be friends with him, I would also say that fairly effusively. In at least two notable cases, I became pretty good friends with the dudes in question. (Both of them, oddly enough, are professors of philosophy. Or maybe that's not odd — maybe they could think through the situation and realize that, tiny momentary disappointment aside, a friendship might be a beneficial thing.)

In another case, however, I was aggressively — and rather defensively — turned down for a friendship by a guy who said, "Since you're not attracted to me, I don't feel comfortable hanging out. I have enough friends. I'm looking for a relationship." Ohhh ... kay. (For the record, I didn't tell that guy I wasn't attracted to him; I said I hadn't quite felt the necessary ineffable spark.) Really, fair game to him, I suppose: I understand how his pride might be a little tarnished. But maybe he could've handled it with a little more savoir faire.

(Side note: I recently saw the man in question at Trader Joe's, and we made eye contact, and I was thinking it might be a nice opportunity to normalize things — until he ran for the frozen-foods aisle.)

But in the case of the God-Believer, I had not been asked on a second date. After we'd gotten together for drinks, he did follow up with a nice email — but it didn't contain an invitation. So I wasn't sure how to handle it. I wondered if he thought I wasn't hot enough, or smart enough, or whatever — if he was picking up on some fatal flaw o' mine. My vanity nearly got the better of me. I thought that if the God-Believer didn't like me, well then, I didn't like him either. So there! In that way, I was being kind of like the Frozen-Foods Aisle Sprinter.

As I was getting ready to skip town, however, I decided, what the hell, I'd drop him a line. If I didn't hear back, surely it would slide right off my back ... and into the Atlantic Ocean.

So I emailed him. And right away, he wrote back, saying, "I'd love to be friends!" He even went as far as saying he thought I was totally cool — and that he liked my writing. Really, he could not have been nicer. It was delightful. We're gonna hang out as soon as we're both back in New York. (He's about to head off on an international jaunt.)

Lesson learned is: Nothing ventured, nothing gained. I know it's not always easy to put your ego on the line and risk a rejection, even when it comes to friendship rather than sexy love — but a lot of times, the risk is worth the reward. And as Virgil said: Fortune favors the brave!