If NBC ever decides to recast Alicia Silverstone’s role in Miss Match, they might want to give me a call.

While I was having lunch at the food court at Century City mall, a guy saw me talking to a woman from my office. About five minutes after she was gone, he came over to me, very tentatively, and started asking me about her. He was a good-looking guy, probably in his mid-40’s (which is about the same age she is), tall, with a bulky frame, blond hair and a boyish, slightly nerdy appearance. Somewhere between Dick Gephardt and Jim Gaffigan.

I understand that there are two ways to read this: “sweet and charming” or “creepy and disturbing”. Please take my word for it when I say it fell squarely on the “sweet and charming” side. He was very shy and modest when he approached me, and the fact that he waited so long after she left before he came over to me makes me think he was debating it in his head for a while.

But I couldn’t really help him, since I didn’t know whether she was married or involved with anyone. (It’s a sad commentary on how little gossip I’ve picked up around the office, I know.) Luckily, a few minutes later, she walked past again, and this time he made eye contact and quietly said, “Hello”. I held up my hand to motion for him to check for a wedding ring.

No ring.

He walked back over to me, newly optimistic. I asked him to give me a business card that I could pass along to her. “Maybe she’ll remember me from when I said hello,” he said.

Then he got up and left, and I continued eating my lunch and reading the newspaper.

About fifteen minutes later, he was back. “I changed my mind,” he said. “I don’t think you should do it.” He told me he was nervous about what she might think, and he didn’t want to make her uncomfortable. He thought maybe he was being too forward. I assured him that passing along a business card to a complete stranger through a third party was actually the opposite of forward. I promised to handle the situation delicately, and he smiled and left.

At this point, I was not only going to give her the card, I was going to make sure she called him. I mean, how sweet was this guy? He probably got all the way back to his office before having second thoughts. Then, the more he pondered what might happen, the more he panicked. Maybe she’d think he was creepy for hitting on a complete stranger. Maybe she’d think he was a wimp for not talking to her directly. Or maybe I was the jerk. Maybe I’d run back to my office and mock him. “Remember that guy who said hello to you at the mall? Was he a tool or what?” He must’ve weighed the possible humiliation of her response against the actual embarrassment he’d face from asking me for the card back, and he finally decided the latter was the better option.

This was not a man who tried to pick up women in food courts on a regular basis. This was a guy who was clueless about dating, who had clearly decided to engage in a rare act of boldness. Maybe he was a lifelong bachelor who had been really lonely most of his life, and he was tired of waiting for love to find him. Or maybe he had married very young, and after fifteen or twenty years of marriage, his wife had left him or died in a horrible accident. It could be that this was his attempt to take his broken wings and learn to fly. (I love making up entire psychological profiles of complete strangers.) Whatever the case, I was like Alicia Silverstone in Miss Match… or come to think of it, Alicia Silverstone in Clueless. I had a project.

So I went back to my office and knocked on the woman’s door.

“Hey, remember that guy who said ‘hello’ to you at the mall?”

“Yeah, he practically leaped out of his chair.”

“Well, he asked if you were married.”

She smiled and blushed and looked away nervously. Could it be that he had her at hello?

She told me she wasn’t married, but she vaguely alluded to a kinda sorta boyfriend who maybe, well, you know… Yeah, I know. Everybody needs a way out of an uncomfortable situation. There was no boyfriend.

“He was really sweet,” I said. I’m so shameless.

By this time, a small crowd of catty co-workers had gathered. (I should’ve closed her office door. Her embarrassment was clearly my biggest obstacle here.) Everyone had a question for me. “Was he cute?” they wanted to know. “Was he weird?” “What does he do for a living?”

We all agreed that she should call him. But she was unconvinced. All she would give me was “I’ll think it over.”

I was pretty sure she wasn’t going to call. She’d think about it, for sure, but she’d debate it and debate it, holding onto the card day after day, and then one day she’d decide the window had closed and just throw the card away.

I felt terrible for the guy. I knew he was going through the hardest part right now: waiting for a response. And I didn’t want to leave him hanging. So I decided to email him. (I’d made a photocopy of his card before I gave it away, of course.)

Hi, —

I’m the guy you spoke to outside at Century City today. I just wanted to let you know I talked to my co-worker when I got back to the office. The good news is she’s not married. She remembered you from when you said hello, and she thought you were a very good-looking guy. [I debated this wording for a long time. I was afraid “very good-looking” wasn’t the kind of thing men normally said to each other and would seem suspicious, but that just “good-looking” sounded perfunctory and unenthusiastic, while also being the kind of thing men didn’t normally say to each other. But I figured the most important thing, if he was really getting rejected here, was to boost his self-esteem, so I ultimately decided to be as flattering as possible.]

The bad news is she IS dating someone, although it doesn’t sound serious. Sorry I don’t know the full story there, but she said she might be open to calling you.

I put in a good word for you and said you seemed really nice, so I’ve got my fingers crossed for you. Good luck!


He wrote right back to thank me and tell me he had his fingers crossed for me as well. (Uh, sorry, bub. I’m taken.)

I was glad that I had done my part and satisfied that even if they didn’t fall in love, that both of them got a little boost out of the situation. That was really all I could hope for.

Then she called him.

That was five years ago, and this weekend, they’re getting married. I’ll be the best man, and I couldn’t be more excited for them.

Okay, that’s what I hope to be writing five years from now. At this point, they’ve only had one date. (Sorry I tricked you. Don’t I stink?) But the day after the date, I ran into the guy at the same place where I’d seen him the first time. He stopped to thank me and to tell me that he thought things had gone well when they’d gone out. “We like a lot of the same things,” he said, “like the outdoors”.

Ah, the outdoors. Of course they like it. That’s where they met.

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