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Miracle Max from The Princess Bride

Maybe you’re only Mostly Gay.

Dear Readers, I promise a work or friendship or health or family question tomorrow, I swear, but this came in over the weekend and I think we can answer it pretty quickly and keep this week’s theme going.

Ahoy, Captain!

I’m another wayward really insecure dude with a lady problem. But I think it might be a moderately different kind of lady problem than you usually deal with. I hope! (Ed. note: SRSLY)

My parents always taught me at home that expressing any kind of attraction to a woman was wrong, because women are too pure for that- but they were so busy losing their shit over the idea of hetero sex, they didn’t even imagine other kinds. I was proudly out as gay since the end of high school. I had several boyfriends in college, some of which I was reallyy serious about. I know I like men. A lot.

I think it is obvious where I am going with this- I then fell HARD for a female friend, in the last semester of college, and it was requited. I can’t even describe how much I like this girl, Captain … I kind of want to pull a Tom Cruise and shout on national television about how much I love her. I totally get that I sound like an idiot. But she’s amazing and I am hella proud just to be her friend, let alone date her.

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Miracle Max from The Princess Bride

"It would take a miracle for this guy take you out for an M.L.T."

Hello, Awkwardeers, I’ve had the good problems of paid freelance work, social fun times with friends, and trying to get a movie project off the ground, so posting has been and will continue to be spotty.

First, I’d like to signal-boost this post which perfectly sums up everything I hate about the idea of the Friend Zone. We all get crushes, right? And sometimes those crushes are on our friends, or we get crushes that turn into friendships. If your friends are awesome, and you’re with me on the “don’t date people who aren’t as cool as your friends” train, it’s bound to happen to you sooner or later. Describing that as “The Friend Zone” implies that you feel a sense of entitlement towards that person and think they owed you something different. If it’s not a friendship that sustains itself once the possibility of getting laid/loved is off the table? Simple. Don’t be friends with people you don’t value for their own sake.

Second, this question came in as a comment on the “A Shy Guy Caught My Eye” post, but I think it deserves its own answer.

Hi Jennifer

I read all of this and thought you gave great advice. So i wanted to ask for your advice. I really like this super awkward shy guy. I’ve liked him off and on for 4yrs. I’ve tryed to talk to him threw text and facebook, for about a year. but he only gives me a few word answers and doesn’t convo back to much. Also last summer we hungout one night and drank a few beers and ended up making out. Well we sat there for alittle bit talking and he was so nerves he keep ripping up the grass we were sitting on. And he told me he liked me for the last 6 months. Well i made the mistake of saying i had liked him for the last 3 years. But i ment to say i liked him off and on for 3 years lol. He was like “Really that’s along time” then i ended up writing him the next day and pouring out my heart (like you said not to do above) (I pretty much did everything above lol). Well he never wrote me back. So I can’t tell if he likes me.

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