Is it OK To Go For People Who Have A History With Your Friends?

Guys have a major loyalty

code when it comes to being with girls who have dated or hooked up with their


I've had my horrible

moments as a friend, like one night in college with my friend Jay. We were sitting in a diner at the end

of the night when a gorgeous girl from Rhode Island (that's the only thing I

remember about her) straight up sat down at our table and told Jay:

You are beautiful, you

have to come home with

But I told him he couldn't

leave me. Perhaps it was because I

was visiting him at his campus and I didn't want to wander around alone. Who knows the reason, but he yielded to

me and told her he had a visitor and couldn't leave me alone.

The next morning I woke up

with morning wood (that strange phenomenon where guys wake up with erections),

and I thought to myself:

Damn, it would have been

nice to hook up last night.

Then it dawned on me how I

had ruined Jay's amazing opportunity. I apologized to him and told him he totally could have gone off with

that girl. He just shook his head

and said:

I wish you could have told

me that last night.

In retrospect most of our

guy friends actually blame Jay for his decision to listen to me, despite my

behavior that my they classified as "girly". In any event, Jay showed major loyalty that night over the

chance to get lucky.

Recently, I was really

into this girl who lives in Hoboken, NJ. Hoboken is a short train ride to NYC, but it's still a major pain in the

ass to get to for Manhattanites. Remember, though, when you're into someone you'll go out of your

y. But on one occasion

when I asked this girl to meet us the upcoming weekend, she said:

Bring Justin.

He's really cute.

My heart sank. She was into my best friend/roommate.

Everything blew up in my face.

But Justin knew I liked

her. He never flinched, even

though she was really cute. He

would say:

That girl is


I don't see what you see

in her.

He never asked me to bring

her out, never acted like he was into her. He never sat me down and said:

How would you feel if I

hooked up with her?

And, the one time they got

left behind at our apartment during a party, I got a text:

How could you leave me

with her?


To Justin, an opportunity

with a girl that his best friend was into just wasn't an option.

Even crazier—I was out

with Justin one night when we ran into a girl that our other roommate/friend

(he wasn't with us) had been seeing. The girl came up to me, and whispered the most frightening, body-contorting

things she wanted me to do to her in my ear. In just a few moments, she had reduced me to a Catholic

school girl with her desires. My

fear of her porn-style wishes aside, I knew I couldn't do it because of her

history with my friend. Not an


My younger sister's

serious boyfriend in college came out of stealing him from one of her best

friends. While he was dating her

friend, she hooked up with him. He

eventually broke up with my sister's friend and started dating my sister and it

grew into a long-term relationship. There were major problems between my sister and her friend after

that. Eventually they worked

things out and they are friends again. My sister has since broken up with that guy.

This might be the crux of

the friendship versus romantic relationship thing: your friends are the ones that will be around forever, and

boyfriends/girlfriends will come and go. As soon as we get fixated on one person and believe they are the one,

then we start getting into trouble: we don't care what consequences there are.

Guys tend to have a

lots-of-fish-in-the-sea attitude. They also are the ones who have to do the pursuing most of the time, so

there's an in-the-trenches camaraderie where they all kind of pull for on

another to succeed with girls.

What is the female dynamic

with compromising friendships through dating? In your friendship duties, are you more prone to keep a girl

from going off with a guy than encouraging her? Have you ever considered dating a guy who has a history with

a friend of yours? Do you agree

that if you avoid thinking of someone as the one, it keeps you out of


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