It’s hard to know when you’ve really hooked a girl. Is it when she first laughs at one of your jokes? Or after that first kiss goodnight? Or, maybe, is it the first time you have this timeless romantic exchange…

Me: So, would you rather date me, or a homeless person?

Her (long pause): At this point, I’m really not sure.

That’s when you know you’re in love. How do you get there? Read on…

I had been on three dates with Rosie, and for the fourth I wanted to spice things up a little. We’d done drinks, dinner, and she’d come over to my place to watch a movie. The best thing about inviting a girl to your place to watch a DVD is that you might as well ask, “wanna come over and make out?” You never actually watch the DVD when you ask someone to come over and watch a DVD. What, I’m going to sit on a couch in private next to someone who’s interested in me and has breasts and just stare at a TV screen? I don’t think so. We should just change the phrase “wanna match a DVD?” to “wanna go to at least second base?” But I digress…

So, in an effort to show Rosie that I’m not a complete horndog, I invited her to a nice, respectable afternoon at a movie theater. With the old folks, and the kids, and the matinée prices (I gotta get something out of the deal, right?). Not only that, but I tell her to pick whatever movie she’d liked. What a wonderfully sweet and considerate idea, right? Right. And then she picked My Sister’s Keeper.

Please kill me.

My Sister’s Keeper is for all the people who’ve loved Cameron Diaz’s fine comedic work, but were wondering how she’d do in something more serious, like, say, playing the mother of a girl dying of Leukemia. The answer to that riddle, incidentally, is terribly. She does terribly as the mother of a child who’s dying of Leukemia. So bad, in fact, that at a certain point, people in my theater started rooting for the Leukemia. “Come on, take her already! Don’t make her sit through another Cameron monologue – she’s just a child!” I didn’t expect Rosie to pick such a, well, bad movie for our date, but I offered, so it serves me right. And looking back on it, My Sister’s Keeper was easily the highlight of the afternoon.

After finishing the film, Rosie and I decided to get a drink, in the hopes of forgetting what we’d just been through. On the way to the bar we walked by a homeless man who asked for change. She stopped and gave him what looked like a handful of quarters, I gave him…nothing. Rosie waited, as if the message sent from my brain to my hands telling them to take out dollars and hand them over just hadn’t arrived yet. Finally…

Rosie: Do you not give money to homeless people?

Me: Uh…

…which is an awkward enough conversation without having to do it immediately in front of an actual homeless person. So I tried to keep walking a little bit ahead, out of the Artful Dodger’s earshot, but Rosie wasn’t having it. Turns out the sort of person who wants to see a movie about kids dying of Leukemia is also the sort of person who will interrogate the ever-loving shit out of anyone who doesn’t hand over their wallet to the first dirty individual they find lying in the street. Who woulda thought?

The amount I give to charity. Daily.

Rosie (getting louder): Come on, you can spare a little something…

Me (getting quieter): I give to charity, I just don’t believe in giving to people on the street.

Rosie: Right, sure you do. Give him some money!

When you’re on the precipice of an argument outside, you’re natural instinct is to go inside. “Come on, people are looking at us out here, let’s go inside.” And, when you’re on the precipice of argument inside, you feel like you’ve just got to get outdoors. “Come on, everyone can hear us in here, can we just go outside?!” I desperately wanted to get Rosie in the bar, while she wanted to harass me in the street. I won, but that would be the only time that day. It’s alright, I’m used to it…

Rosie: It doesn’t bother you that he’s hungry and you could help him get food?

Me: No, it bothers me that he’s thirsty and I could be helping him get booze. I heard an interview on This American Life saying that there’s countless soup kitchens in New York-

Rosie: Oh, so NPR says it’s fine to ignore the homeless, so that’s what you do?

Ira Glass would totally have my back

Me: No. (Thinking: Yes.)

(And, yes, I recognize it’s an annoying liberal douchebag thing to do to say you heard something on public radio that allows you to be selfish and piggy, but, well, I really did hear it.)

Now everyone in the snooty little bistro that, I might add, makes a rather ironic choice for my bleeding heart date, was staring at us. At that point, I would’ve killed for another hour of My Sister’s Keeper. Give Cameron another daughter and this time let her have palsy! She continued…

Rosie: Look, it’s just…I feel really strongly about homeless people. They need our help, and so many people won’t help them just because they assume they’re drunks. But they’re not always…

And that was, to be frank, when I kinda zoned out. I mean, this was just weird. Rosie was a cool girl and all, and I’m genuinely as guilt-ridden as the next liberal, but our first fight being about homeless people was a little too much. She kept going on and on, and I kept not listening, so as it became clear that she was going to stop talking any moment, I had to come up with an answer. I had the chance to be sensitive and supportive and apologize for my actions and my “misunderstanding”, or I could be snarky and obnoxious. I think you remember how this one turns out…

Me: So, would you rather date me, or a homeless person?

Rosie (long pause): At this point, I’m really not sure.

That night there would be no watching of DVDs.