Tip No. 5: When you think a girl looks pretty, say it.

“But don’t reference the thing that might reveal you are aware of the backstage process: e.g., say, ‘You look gorgeous tonight,’ not ‘I like how you did your makeup tonight.’ Also, a compliment means less if you compliment the thing and not the way the girl is carrying it off. So say, ‘You look so sexy in those boots,’ rather than ‘Those boots are really cool.’ I didn’t make the boots! I don’t care if you like the boots’ design! We are magic to you: you have no idea how we got to look as good as we do.”

I have a lot of female friends, and when at all possible, I try my best to remind them how terrific they are. I don’t get to see much of them these days, as most of them live back in Ontario, so I end up getting a tad overwhelmed by their fabulousness in person. I try not to be too forward or creepy about it; they’re my friends, after all, and I’m not telling them that I find them attractive because I have aims on them physically. “You look so sexy in those boots,” for example, is not a sentence I have much cause to utter in good company. But I have no trouble letting them know how great they look.

Kaling’s also talking about dating, and flirting in general, and I haven’t been doing much of either lately. That’s not to say I don’t want to, and that I haven’t been thinking about being a bit more adventurous with flirtation. The mere fact that I’m not ashamed to tell a girl she’s pretty makes me a decent flatterer. I think most guys either undercompensate and clam up, too fearful to say anything because they don’t think they’ll say the right thing, or overcompensate and come off as total sleazes, even if their intentions are noble.

Anyway, I’d like to think I’ve become more adept at letting a woman know that I find her attractive without being too cheesy about it. There’s something endlessly classy about a guy who seems to let his macho guard down for a second because he’s overtaken by a woman’s beauty. Honesty is key, seconded only by brevity. And as Kaling says, being too specific can drain the sentiment from the moment completely. Words of appreciation travel far, especially if you’ve been in a relationship for a while. It’s important not to let things go unsaid.

[youtube=http://www.youtube.com/watch?v=wMbCLB2vLkU]

That about wraps up the Awesome Guy Challenge. After over a month of travelling, I’m heading back to Vancouver on Saturday, where I’ll be doing more dishes, letting more people onto elevators, and smelling more like James Franco than I ever have before. Here’s to an awesome new year.

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