Letters With Boys

Bridget and Kai, Week 4 - October

Hey Kai,

Mem just told me that Gray asked her for ratings on his performance Saturday—and not JUST his performance, but even his LOOKS! Mem, being the minx that she is, actually obliged. I am far too kind a soul to ever rate people based on their appearances, but I do think you might benefit from a little bit of gentler feedback.

Regarding your wardrobe: excellent job. You took my instructions very literally. My only complaint would be the tennis shoes, but I think that’s on me for not having been specific enough. For future reference, never wear tennis shoes on a date!

Regarding your conversational skills: You are a fun and easy person to talk to, and I could tell Tally felt that way, too, so props there. But where is the FLIRTING, Kai? You talked to me and Mem the same, exact way you talked to Tally. Did you stop crushing on her? Or are you just that careful?

If you need an example of how to flirt with a girl, look no further than your buddy, Gray. Guy was smooth as butter with Mem. I have never seen her so taken with anyone, and that includes Matt Hirsch, who she dated for like eight years. And why was she so taken with him, you might ask? You know—besides the obvious, bad-boy good looks? Well, he made her feel like she was the only person in the room. In the world, really.

So, basically, you need to work on your flirting skills. Keep in mind who Tally’s pen pal is, what he looks like, and the fact that he’s already tried sleeping with her once. 

Other than that, job well done.

Looking forward to Wednesday!

Love,

Bridge

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Bridge,

I just did a literal facepalm when I read your letter.

I’m really glad I have you, buddy. I don’t think anyone else would ever have been this honest with me, and apparently I sorely needed the feedback.

Of course, I didn’t stop crushing on her. She’s hands-down the coolest girl I’ve ever met—probably the coolest one who’s ever lived. (No offense. You're cool, too, Bridge—she's just more "my cup of tea," as they say.) It makes me want to drown myself in boiling lava that I didn’t make my feelings clear to her. 

Okay, maybe that’s a little dramatic. But your reminder about Ezra certainly didn’t help.

At least I have tomorrow, right?

Any words of advice on how to improve my flirtation skills before then? Besides “channel your inner Gray,” which is advice I’m pretty concerned about taking?

Thanks as always,

Kai

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Kai,

Despite being good at practically everything, I’m actually not particularly good at flirting, so I just asked Mem, who is very good at it, when she wants to be. (Like Saturday.)

MEM’S RULES FOR FLIRTING:

(1) Compliment the person once, and only once, on something you’ve never complimented them on before. Something that will really make them feel noticed and appreciated.

(2) Make fun of the person enough to make them giggle and blush, but not enough to actually make them feel bad about themselves.

(3) Let yourself get caught looking at the person, but then look away quickly, as if you’re embarrassed. This can happen more than once, but not more than three times.

(4) At some point in the interaction, touch the person lightly—on the arm, for example, or the shoulder. This should be innocent and quick.

(5) Smile and laugh, even when it’s hard to.

That last one made me feel a bit sad. I think it’s hard for Mem to smile and laugh at boys these days. It’s different with us, but with them…

Well, she’s scared. But I won’t get into all that.

Looking forward to tomorrow. I believe in you!

Your Biggest Cheerleader,

Bridge

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Cheerleader Bridge,

Thanks for the help with the flirting tips. I have a feeling you’re going to tell me I did a s**t job of it again, but let me know. I think I did most everything on the list, but I can hardly even remember. My head kind of turns cloudy when I’m around her.

It’s funny—in that way that’s not funny at all—because yesterday reading your message about Mem made me feel really sad for her, and then seeing her at the game, well, it made me feel really sad for her. Is she okay? She was so different from how she was Saturday. Poor Gray seems distraught over it, like maybe he did something wrong. 

How are you doing, by the way? I hope you know that I don’t want or intend to monopolize all of our valuable letter-writing-and-reading time talking about Tally. You’re my friend, and I care about you, and I want to talk about you, too. 

Love,

Kai

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Kai,

Okay, so, here’s the thing.

Tally’s going to some pro soccer game with Ezra in NYC this weekend.

I feel shitty telling you that, but like you said, we’re friends, and I’d rather you hear it from me than from someone else.

I think you did a great job flirting, for the record. She didn’t say anything one way or the other about you, but that’s normal for Tally. She didn’t even really say anything about Ezra, either—just that she was going to a game on Saturday. (And that she’d be back by Saturday night, if it's any consolation?) But we pried the details out of her.

For what it’s worth, Tally really likes sports. So it’s possible she’s just going for the free ticket.

As far as Mem goes—she’ll be okay. She’s going to the city, too, this weekend, for a stupid non-anniversary celebration with her ex-boyfriend that’s going to make her severely depressed. I think her attitude at the game was just pre-depression depression. That, or Gray. He’s the first guy she’s developed real feelings for since… well, anyway, it’s hard for her.

Why don’t you and I hang out this weekend? Both my girls are ditching me for NYC, and you don’t seem to have much of a life, so why not, right?

Let me know. 

Bridge