Catherine Townsend: Sleeping Around

He was intelligent, charming and ugly

A while ago, I met a shy and hugely successful director, Documentary Boy. Although he was one of the least attractive men I had met, he was also charming, highly intelligent and had a killer self-deprecating wit. He had a face like an otter, but I was smitten. And in some dark part of myself, I felt completely safe, because, despite his success, I was confident that someone so weird looking would never break my heart.

So, it was a something of a surprise when, a few weeks later, he disappeared claiming that he "wasn't sure if he wanted a girlfriend" because "things were so crazy" with his career. Then my friend, Amy, saw him at a party with his arm around a stunning blonde. As it turned out, my rough diamond was getting laid right and left - because every girl was using the same logic. He was more of a player than the gorgeous guys. Dating is sometimes like shoes. If a girl picks up a pair that no one else wants, other girls will start circling wondering what they are missing and suddenly they are the hottest thing in the store.

I thought of DB this week after my date with The Journalist. We met at a friend's party when he charmed me with his war stories about dodging bullets in Kosovo and Afghanistan. He was no oil painting, and several inches shorter than me, yet by the time we left the restaurant, I was contemplating taking him home. It's the Mr Rochester complex: women think that by "settling" in the looks department, the guy will compensate in other areas - which is not always the case.

Amy, who works in fashion, said she went through the same thing with a guy a few years ago. "He was overweight and a terrible dresser, but he made me laugh," she says. "He used to act really insecure, telling me that everyone was sure I was going to break his heart. So when he told me it was over, I was shocked. I was like, 'Hang on a minute - you're dumping me?'"

After dating several metrosexual men, there was something liberating about The Journalist's "to hell with it" attitude. He ordered rare steak and neat Scotch - unlike my recent date with a super-fit former ballet dancer, who spent the better part of two hours discussing the difference between good and bad carbs. The Journalist and I never ran out of banter, until he kissed me in the rain. He hailed a cab and like a perfect gentleman offered to drop me home. Things didn't start to go downhill until my marathon training cropped up and he said something amazing. "Yeah, you're pretty fit," he said. "Which is great, since I never date women larger than a size 12." Eyeing his not inconsiderable girth, I laughed and asked if he was kidding. He adopted the look of a deer caught in headlights. I left him at my door.

The next day, I meet my friend Michael and he's not surprised. "Women are less shallow when it comes to looks, which means that less attractive guys think that they can rely on money, power or personality," he explains. Is that why women who look like Elle MacPherson worry that "looking fat" will impede their pulling power, while men with Donald Trump-style comb-overs wink confidently at their own reflections before heading off into the night? Yes, nods Michael.

All things being equal, many women would choose intelligence over beauty any day. Alas, I never got to find out with The Journalist. He's off on holiday to New York tomorrow for 10 days with several female "friends", but he did text me thanking me for a great time and calling me beautiful. Maybe I was being a bit unfair - after all, he was just being honest. And he is a charmer.

But his departure is convenient, since I'm having drinks next week with an Australian banker whom I met after my shoe slipped on to the tracks and under a Tube train at Earl's Court station.

c.townsend@independent.co.uk