An innovative pick-up line (scenario?)

Well, he was persistent, I'll give him that much...

The other day I was heading out to get my haircut and while I was heading south on Spadina I heard someone trot up behind me and felt them tap me on the shoulder.

I turned my head to see who it was, I kind of assumed it was someone I knew, but instead I was met with the sight of a grinning stranger. A pretty cute, well-dressed, grinning stranger - not the kind of Toronto grinning stranger that I more often end up running into where you're pretty sure their meds aren't quite balanced properly, if present at all (god, our social support systems don't work – but that's a rant for another day).

Stranger – Do you mind if I ask you a question? It's a serious question, I really am curious.

Me – Uhhh, okay?

S – Why are you carrying two bags?

M – Oh. Well, one's my purse, and one's my laptop.

S – Doesn't that get heavy? Why don't you get something smaller, I just got a Mac Air, it's great, you should get one of those.

M – Well, sure, but this one works and is 7 years old, so by now it's free, so I'll stick to it for now.

I sort of smile, nod and turn away and keep walking. He keeps pace.

S – Can I ask you something else?

M – um. Sure.

S – What are you doing right now? (it wasn't until he asked this that it dawned on me what the hell was going on)

I'm always pretty bad at this part, the part where I realise there's a good chance I'm being hit on. I get kind of stammery, or I over-compensate by being really really aloof. I think in this one I went the aloof route.

I told him I was off to get my haircut, he said my hair looked good I shouldn't cut it. I told him it was 'cause I had a photo shoot the next day. He decided that meant I was famous. I assured him I wasn't.

This went on for a reasonable amount of time. He initially tapped my shoulder north of College, my hairdresser isn't until almost Dundas (sorry non-Toronto folks, that's a little over half a kilometer, not long on it's on, but a reasonable distance in the 'walking with a stranger' scheme of things...), so probably more than 5 minutes.

During our time together he talked about how much money he spends on art, he talked about his really expensive computer, he tugged on his expensive clothes to draw attention to them. It was like what he really wanted to say was “Hey, lady, guess what? I have money. Isn't that exciting. Doesn't that make you want to hang out with me?”

It, of course, had completely the opposite effect.

It made me feel kind of sorry for him actually, 'cause it felt a bit like he was insecure and thought that money was what he could bring to the table. In truth, he seemed pretty nice, was a good looking guy, and had the guts to walk up to a stranger and talk to them.

Makes me think that he probably has more going for him than he thinks he does. I probably would have found out more, except I was busy high-tailing it to my hairdresser and making sure I was leaving fast enough he couldn't ask me for my number.

Like I said, I'm really bad at these things...