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I've been on-and-off friends with benefits with this guy I knew in high school but I go to school in Fort Myers and he lives in my hometown, Miami, so we only hook up and stuff when I come home for the holidays, etc. But when I'm away we actually have really good, wholesome conversation, and we actually are really compatible. I don't wanna be one of those girls who falls in love with her friends with benefits, and I also don't know if he feels the same way, but I could totally envision us in a real relationship, but I'm also worried because he hasn't been loyal to other girlfriends he's had in the past (I've heard from rumors). I could be completely off base but do I shoot my shot and risk the FWB relationship or losing him from my life? I'd rather have him as a friend than lose him forever, y'know? Ugh. So complicated lol

The number-one rule of a friends-with-benefits situation is that it can only work if neither of the "friends" is more interested than the other. I mean, it's so common it's become the very plot of movies like "No Strings Attached" and "Friends With Benefits."

That said, if you're starting to feel a connection that's deeper than friendship with the guy you've been hooking up with from home, chances are it's only going to grow. So, you have two options: One, stop hooking up with him, keep the talking to a minimum, and move on or, two, tell him how you're feeling.

Before You Take The Leap

Before you make a decision on what to do, though, can you picture him in your future?

I know this question might seem intimidating, but since you have been friends for a while, you likely know a lot about him. Before jumping to express your feelings and risking anything, ask yourself these questions:

• Do I trust him?
• Would he make a good boyfriend?
• Does he have what I am looking for?
• Does the distance matter?
• Can I see him hanging out with my friends?
• Would he get along with my family?

The Risk

If these questions help confirm your strong feelings for him, I vote that it's best to let him know.

Whether you expected it to happen or not, you developed feelings and you should not beat yourself up about being "one of those girls who falls in love with her friends with benefits." It happens! And for all you know he could be feeling the same about you! Because trust me, guys don't put time into nurturing long-distance friendships without some sort of interest — even if it's just sexual.

Because your feelings are involved, I will always vote that it's best, to be honest. I say this because if you're not honest, you're only hurting yourself by staying quiet and continuing to talk as you grow fonder about him — unless, of course, you cut him out of your life, but why do that if you don't have to? Talk to him!

It doesn't have to be a whole "I want to be your girlfriend" conversation. Ease into it by dropping hints about how much you enjoy talking to him and wish you could hang more. See how he responds and take it from there in baby steps. One day you might even want to ask him to visit you at school or you could plan a random weekend to go home and actually make plans other than hooking up — a date, perhaps? (But you don't have to call it that... yet).

Since you've been friends for so long, I don't think you should rush the process.

Feel these things out first — you can do it over a few conversations or even a few weeks, whatever feels right for you — and then you can open the doors a little further by asking him why he talks to you despite the distance. See his response and respond accordingly! If he's not giving you the answer you want you can decide to drop it or pry further. I would say at this point you should tell him how you're feeling because he, one, might not be picking up on your hints (boys... ugh) or, two, might be too scared to bruise his ego and be the first to let you know he likes you, too.

The Possible Outcomes

1. He tells you he is only interested in you as a friend
2. He tells you he has developed feelings as well

The Reward

No matter the outcome, being true to yourself and honest about your feelings is the strongest thing anyone can do. The reward for doing so, regardless of the outcome, is feeling free and empowered to express yourself. At the end of the day, being vulnerable is scary, but it is a beautiful thing. Best case scenario, your FWB says he feels the same way! Absolute worst-case scenario? He wants to remain friends.

Either way, you get to decide where to go from there and that's a powerful thing. The ball is in your court.

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