Friends with Benefits; Is there a chance he could fall for me?

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Hi Guys,

What do you think are the chances of a FWB falling for you? I’ve had a FWB relationship for five years. We talk all the time, argue most of the time, have incredible orgasmic sex, have stood by each other through good and bad times. But we just can’t talk about our feelings. So crazy and I don’t know how to deal with it.

I’m not the the kind to pour my heart out to get turned down. After five years if he wanted something more he would have asked hey?

He has said things like we should get married and live in a caravan and have 100 children. Weird and no thanks. But why joke like that? And he has said we argue like a married couple. He has said he loves me and then moments later I’m back to being his best friend ever.

I don’t get it. I can understand that he is not in a position to provide for my child (7) and me. But I’m not asking for that.

I’m 29 and he is 33 by the way. And I have had a relationship during this time and he has slept with other girls. We just always go back to each other.

So any ideas which direction I should take? I don’t want to waste time. But don’t want to lose one of the best things that has crossed my path.


Dear Cassidy,

Thanks for your question. Please watch our video on this topic. “Friends with Benefits”  This will answer most of your general questions about a “Friends with Benefits” (FWB) arrangement.

As far as your specific question, it does seem like if he wanted to take this relationship to the next level he would already have tried, or at least the two of you would be discussing it. But having a five year FWB arrangement has given him no reason to do much else. He’s getting regular good sex with someone he cares about a lot; he has no other responsibilities, no other demands on his time; he’s pretty much free to do whatever he wants and he knows you’ll still be there. We don’t see the incentive for him to do much else, at least from his perspective. Do you? (Note: We do think that having a committed relationship is enough incentive for many guys.)

Your daughter may be complicating matters a bit, but it’s not like he’s unaware of her. We know you said you’re not the kind of girl who pours their heart out to a guy, but we do think you need to talk to him about how you feel. You say you don’t want to lose one of the best things that has crossed your path, but what do you really have now? You don’t really have a relationship, you don’t really have this guy? You have semi-regular fun together and that’s it. If you truly want more with this man, then talk to him about it. Tell him how you feel, and what you want, and ask him where his head’s at. If he says he’s unsure, or just doesn’t know, then it’s time to move on, because he’s had plenty of time to figure out what he wants. Believe us, he knows even if he doesn’t say it.

This may or may not turn out the way you hope, but at least you’ll have some answers and know you did everything in your power to make things work. And you’ll have no regrets, which is so important.

Good luck. We hope this works out for you. Please feel free to ask us a follow up question, or another question. Leave us a comment in the comments section below.

Also, you might enjoy our “Relationship Memoirs” page, especially Charlotte Pescale’s “Rebeccas, a memoir.” Start from the beginning with the introduction and read Ch. 1  and Ch. 2. And please let your friends know about us. Thanks!



Read other posts about Friends with Benefits. FWB

The Ex Files: Friends with benefits? 

Are we friends with benefits or does he want something more? 

Booty call or relationship trouble 

Divorced and now online dating: Am I booty call or more?

I suggested friends with benefits; did I just dig myself into a hole?

Friends with benefits; why me?

Friends with benefits? 


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