Joe Masterman

Ever wonder what guys think, how to deal with them, or whether instead of listening to you they just imagine you naked?  Our Real Live College Guy Joe will answer all your questions about men and relationships with wit, clarity, grace, and physical attractiveness (can you tell he wrote this intro himself?) all while imagining you fully clothed!  Well, usually – he is a college guy.

I don’t have a boyfriend, but I have a few guys on my radar, who I’ve either sort of started to date, of have hooked up with, or have just been flirting with, etc., all of whom I think have potential for something.  But now it’s about to be winter break and we’re all going to be in different places for a month at home and not at school!!  How should I leave things before school ends and then what can I do over break so that those don’t all fizzle by the time second semester starts? –Bubbly at Bowdoin

It sounds like you’re in a very lucky position, Bubbly.  Either women are scarce up at Bowdoin, or you’re much more attractive than your fellow female classmates, most of whom are probably moose. 

Ever wonder what guys think, how to deal with them, or whether instead of listening to you, they just imagine you naked? Our Real Live College Guy Joe will answer all your questions about men and relationships with wit, clarity, grace and physical attractiveness (can you tell he wrote this intro himself?) all while imagining you fully clothed! Well, usually – he is a college guy.
 
My boyfriend and I have been together for about two years now, and we have never had any trust issues.  But lately, he’s been spending a lot of time with a friend of his – a pretty girl friend.  I’m trying to think of her as just one of the guys, but I recently heard she has a crush on my boyfriend.  He knows and says it’s not a big deal, but he still hangs out with her.  They have even had dinner together—just the two of them.  I don’t want to be a controlling girlfriend, but is this weird?  How can I tell him I don’t want him to hang out with her anymore?– Edged Out at Emerson

Ever wonder what guys think, how to deal with them, or whether instead of listening to you, they just imagine you naked? Our Real Live College Guy Joe will answer all your questions about men and relationships with wit, clarity, grace and physical attractiveness (can you tell he wrote this intro himself?) all while imagining you fully clothed! Well, usually – he is a college guy.
 
So I have been on and off hooking up with one of my exes for the past three years. I keep trying to either end it or figure out if he wants a relationship. The last time we parted, I thought it was definitely for good. We cut off all communication, and there was a whole sob-fest, final discussion and everything. Well, that only lasted a month. He contacted me one night after I had gone to a party, and everything started all over again. My goal this time was to figure out what the heck he wants! To date or not to date? And if not, why is he keeping me around when he knows I have invested feelings?  - Never-ending at NYU 

THREE YEARS!?!? Are you kidding me? As in one year, except times three? As in about 1/7 of your natural born life? As in longer than the lifespans of most marriages, goldfishes and marriages amongst goldfish?  Three years, Jesús. 
I should collect myself.

Obviously, this guy still has feelings for you. Because in three years, he could have hooked up with, let’s see … one, times seven days a week, times 365, plus a few for holidays – about a hundred billion girls. You can check my math, but I think it’s correct.

Ever wonder what guys think, how to deal with them, or whether instead of listening to you, they just imagine you naked?  Our Real Live College Guy Joe will answer all your questions about men and relationships with wit, clarity, grace and physical attractiveness (can you tell he wrote this intro himself?) all while imagining you fully clothed! Well, usually – he is a college guy.
 
So, my boyfriend and I have been dating for five months, and I really wanted him to introduce me to his parents. He finally gave in, and we are meeting them next week! Of course, now that I’ve gotten what I wanted, I am super nervous. What does ‘meeting the parents’ mean? How should I act? How does he want me to act? Will he care what they think of me? And, most importantly, what should I wear?!
    -Don’t Want to Be a Disappointment at Dartmouth
 
So you’re safari-ing into the habitat of parents (homus parentus boyfriendus), eh? It can be a dangerous place. The parents can be a standoffish species, not accustomed to the presence of young humans ever since their offspring abandoned the nest. If startled, they can lash out with a wide array of defensive tactics, such as snide, offhand remarks about your clothing or extreme drunkenness. Approach with caution, and follow these safety tips for the parental wilderness:
 
Outerwear