The One That Got Away?

On the way back from my meeting in Surrey (via a trip to Debenhams, where I rinsed the credit on my gift card - and then some - on the most beautiful pair of high waisted denim shorts and floaty summer top I have ever seen. Sigh) I had one of those rare chance encounters that leave you wishing you had conducted yourself differently, and so led to a different outcome. Picture the scene: I'm walking down the road when a large (6 foot plus) burly black man walks past me. In a dress. With killer heels and a face covered in garish mauve makeup. As I turn to my right to watch him pass (subtlety never having been my strong point), the man walking beside me turns to his left and does the same thing. We make eye contact, and our conversation goes something along the lines of this:

Him: Um...did you just see that?
Me: Yes.
Him: Was it a.....?
Me: A man. In a dress. Yes.
Him: Wow.
Me: Yeah, not really what you expect to see on your way back from work (or words to that effect).
Him: That's made my day.
Me: (laugh)
Him: Come on, don't tell me it hasn't brightened up your day too.
Me: Quite literally, yes. Did you see that makeup?!
Him: So...have you had a good day?
Me: Er..yes thanks.
Him: What have you been up to?
Me: I've been to Surrey for a meeting.
Him: What do you do?
Me: I work for [insert name of charity]
Him: As in [insert name of corporation associated to charity - not sure why I'm being cryptic..]?
Me: Yes, that's the one (explain what it does)
Him: Wow, I wish I could say I did something charitable, but I'm afraid that would be a lie.
Me: Why, what do you do?
Him: I'm a trader.
Me: Nothing wrong with that.
Him: Where do you live?
Me: Just on that road past the pub. You?
Him: Two roads down on the left.
Me: Well (2 secs later), this is me.
Him: Okay. Bye.
Me: Bye.

It wasn't until after he had walked away that I a) registered he was actually incredibly attractive (tall, floppy brown hair, lovely brown eyes, dressed in chinos and a pink shirt - love a man who isn't afraid to show his feminine side) and b) registered that he might conceivably have been interested, given the amount of questions he was asking (after all, he didn't have to strike up conversation, right?). If I'd had even two minutes longer to assess the situation I might have been bold enough to offer him my number, but the whole exchange happened so quickly that it just didn't occur. At the very least I could have given him my name. I fear my shock at being engaged in conversation by a stranger (with the catalyst being a drag queen) came across as aloofness and he just didn't think I was interested. Either way: Gah, missed opportunity. It's not often a random hottie talks to you in the street, least of all a city trader!