When you’re a New York City guy, you get used to taking cabs everywhere. You also learn pretty quickly how to share a cab with someone, if your stop is on the way to their destination. You consider sharing a cab, even if the date didn’t go all that well. After all, it’s a matter of efficiency. Depending on the location, the night of the week and the time of the evening, you could be standing outside waiting for another 10 minutes in the cold, if you don’t share.

So there I was. It was a second date. I had been on the fence about seeing Amanda (her name has been changed to protect her identity – and rightfully so, when you find out what a cheapskate she is!) again, when I let Marjorie (her name has been also changed, just so as not to create any hard feelings…), our mutual friend “twist my arm” into asking Amanda out again.

Our first date had been nothing spectacular, but it wasn’t a disaster either. It had been dinner on a Tuesday night after work. At least I got a steak – and it was good enough to make a second date.

Our second date was (supposed to be) a step up. Dinner on a Friday night after work – leaving open the possibility that it might go really well and we’d go back to her place for a night-cap since it was a Friday, after all.

Well, that wasn’t meant to be. I let her choose the restaurant. Something frou-frou – didn’t really sit well with my masculine palate. Too many vegetarian options, and the few meat dishes were a little “lite”. She was tired. I was tired. We were both yawning – from being tired AND truthfully bored. She just wasn’t that interesting, and I didn’t feel like putting on my jester hat to keep the conversation going. Sometimes you have to just say, “Check, please”. And call it a night.

It was pretty nippy out. I had a trench coat on – without the heavy lining. I was caught in the dreaded seasonal change – the time of the year when, if you’re not careful, you can wind up with a nasty cold.

And it was just about the time that theater was letting out. All of the taxis would be in Times Square, and the West Side in the high 30’s – a/k/a Hell’s Kitchen – isn’t the most popular place for cabs at 10:45 p.m. So I knew we needed to share.

I was headed to Penn Station to catch a train to Long Island, where I recently moved – while she was heading down to the Village. I asked if she would mind dropping me at Penn Station, and she (reluctantly) agreed.

Cab sharing etiquette dictates that I have to offer to contribute to the ride. But cab sharing etiquette also dictates that, if it is a short ride and it is truly on your way, which this was, you should just say, “No problemo, I’ll get it this time,” even if you know that this is going to be your last date just based on the general feeling in the air.

True, there was that awkwardness, when you both know that this is going no where, but there are still practical matters that have to be dealt with (much the way suburban dates result in the silent ride back to someone’s home…), AND I had just dropped $150 on a mediocre dinner….

Did I mention that I spent the same on our first date – albeit at a better restaurant?! Couldn’t she just pick up the cab-tab?!

In any event, when we were within a block of Penn Station, I reached for my wallet and much to my disappointment, she didn’t stop me. She not only let me contribute to this short ride, but she also let me pay for her entire ride AND then give her a bonus, to boot!

My cab ride would have cost me, had I taken a cab across several avenues and a few street blocks down alone maybe six dollars. Amanda was going much further, and her ride would probably have cost, given the traffic, about ten or twelve dollars had she been on her own. All I had was a twenty. When I pulled that out of my wallet, she said, “Thanks,” and snatched it out of my hand, just as the cab pulled up to Penn Station.

And that was that. 20 bucks and a five minute cab ride later…. That was it. I never saw her OR my $20 again. Which do I miss more? Let me think…!

Moral of the tale – carry smaller bills AND oh, don’t date cheap women!