Will this be more than Friend with benefits?

Dear Guys,

I have a recently separated male best friend of over 20+yrs who helped me through my divorce. He has an arrangement of staying in his home til his youngest is out of school. (He just turned 19.)  My friend has stated that we are okay to have sex but that he’s not ready for anything serious because he hasn’t healed yet. He’s having no sex but with me and vice versa.

I wanted to approach him years ago when we were in the military before either of us were married but I was too shy. Well now that we’re in this arrangement I find myself falling for him again. I told him I think I was in love with him and he said that he’s still not ready and that we are best friends. We’ve had sex once and we both agree we want to do it again and again, to explore. But how do I know if he’s ready for more than Friends with Benefits? His son will be leaving home soon and then he’s getting divorced. So what should I do in the meantime? He calls me to see if I’m okay, since I’ve recently been a single mom and it’s hard but I am falling more and more in love with him. I know he cares about me but from a guy’s point if view, what is he feeling? Will be ever want more? Please guys help me out?

Confused Mother

Dear Confused Mother,

Ever is a long time. So it’s hard to say if he’ll EVER fall for you, but right now, he’s nowhere near being ready. The last thing a guy is looking for after getting divorced—he’s not even divorced yet— is another serious relationship. Usually, he wants to make up for lost time. Which means he’s looking to have as much sex as possible, either with one partner, or many partners. He also wants to enjoy his freedom, and be selfish and not have to answer to anyone. When your guy says he’s okay to have sex but really nothing else, you need to believe him. Having sex with you does not mean he’s falling for you. It means that he’s getting his needs met, physical and maybe some emotional, and that’s all for now.

That said, we’re not saying he doesn’t care about you, or that at some point down the road he’ll want to be with you, but honestly, he’s got a long way to go, and the road could be quite bumpy for you. Typically, Friends with Benefits arrangements don’t lead to more serious relationships. Men usually propose them because they are either in a situation like your guy is in, or they are still looking for the woman they want to be with long-term, but at the same time don’t want to be celibate while they’re healing or searching or whatever.

This is your call, but be very careful here. You’re also forgetting an important point. (Or maybe we don’t have it right.) But if you were friends before the two of you were in serious relationships or marriages, he had a chance with you then and didn’t act on it. Maybe things have changed, maybe they haven’t, but he keeps insisting that he’s not ready and that you’re just friends, instead of saying something like, “As soon as I get my divorce we’re going to be together.”

Overall, we think you’re just going to end up being more confused, frustrated, resentful and  possibly hurt. Sorry, we wish we could be more positive and we sincerely hope we’re wrong, but that’s just our opinion. You must decide how you want to proceed. Have you had a heart-to-heart with him? Have you asked him what he sees for the two of you in the future? Since you’re friends, it seems like you’d have nothing to lose by talking with him. What do you think?

Do you have any follow-up questions or thoughts? Please leave in the comments’ section below. (You must be Logged In to do so.)

Take care,

ps. We hope you’ll let your friends know about us. Thanks!


22 Comments on Will this be more than Friend with benefits?

  1. geminidmn // July 12, 2016 at 10:25 am //

    I too need to know. i met my so called FWB on an online date site October 2015, however, we never met face to face until May 2016. he came to my house and brought champagne and we hung out talked and had sex. now by having sex, i mean he went on to please me for hours before he had sex, his motto is a woman cums twice before he does at all. the second time he was supposed to come to my place but he planned a beach night citing the full moon, he asked if i wanted a fire and so we sat on the beach by a fire under the full moon and then again he did me for an hour. the third time at my place he took me out to eat, we went back had champagne again and then the usual, me me me. we talked more this night than usual, he insists NO CATCHING FEELINGS, but when i went to shower, he stepped in and washed my hair, which i wasnt expecting so i was a bit caught off guard,LOL. we talk a lot, he askes me random questions, then he says what he thinks im feeling and it is all true. we see each other infrequently because he lives 2 hrs away and has custody of his 4 kids. We are going out next month to baseball game.He is so sweet, and hot at the same time, he isn’t HOT in the traditional sense, hes HOT to me. is this normal FWB behavior or is he just so scared he cant move on. he never takes compliments, or believes he is good enuf, body part wise, cause he asked me if it was GOOD ENUF. when I compliment him he says nothing when i asked why he said because he gets them so infrequently he talks them with a grain of salt. when I thank him, he says I NEVER have to thank him. i think he says one thing but his actions say another. HELP!

  2. @Geminidmn…..FWB arrangements don’t typically develop into anything more serious, especially when the guy says, “No Catching Feelings.” That said, fill us in a little more and we’ll think about it. How old is he? You? How recently has he been divorced? How old are his kids? Has he talked about seeing you more? Or anything else like that?

  3. geminidmn // July 12, 2016 at 1:47 pm //

    he has been separated for 3 years his divorce was just finalized this past June 8th. I was under the impression he was divorced, however i know he hasn’t been with her for years. he txt me telling me what he got and how it went down. basically we’ve been txting every day since we began in october. He worked nights so we were txting to 2 3 am, talking about everything, our lives, kids, when i would say something he would ask why or why not, or other ways for me to expand on what i was saying. however, he just went on days, so we talk a bit less since he has to get up at 5 to get kids ready and its an hr from where he lives to work. his kids are 12, 14 17 and 20 the oldest is going away to college in sept. we talk about seeing each other, it just has to be planned so he has someone to watch his younger kids, and we have plans to go to the ballgame next month. he is 47 and he is a few years younger than I am, and I have a 20 year old daughter also. i asked him if age mattered to him and he said NO. I am extremely fit and healthy, i workout at the gym 4 days a week and I am 5 2 115 lbs and much younger looking than I am. he tells me he loves my body and he loves pleasing me and how he daydreams of ways to please me, which i know can be BS but he does. he is sweet, kind, generous, mature, funny so very funny, he is sarcastic like me, we get each others comments and he is well if i could build a man, he is what i would put together LOL, but he has to have some feelings for me, i mean, hes too giving and attentive not to, unless that is just how he is. IDK. if you need to know anything else let me know.

  4. geminidmn // July 12, 2016 at 1:55 pm //

    his ex is an alcoholic and abandoned him and the kids he told me how the whole divorce started and how it went down, he talks about it and i let him because i think he needs to, he was hurt from her constant cheating and that is how my ex and I split, cheating. its tough I know but it is what it is

  5. @geminidmn…….Okay, now we have a clearer picture. You say: He must have feelings for me, otherwise he wouldn’t try to please me? Well, that’s not necessarily true. Does he have feelings for you? Sure, in the sense that he enjoys talking to you and being with you. But there are two main reasons he might be spending so much time pleasing you. 1. He loves having sex. 2. He’s insecure about his “manliness” so he goes overboard to make you happy. The good news is, you’re both about the same age and in the same stage of life. (Mostly) We’d say, if you’re having fun, just go with it. But unless he starts talking about wanting to date you exclusively we’d say keep your expectations on the low side. Does this help? Any more follow up questions?

  6. geminidmn // July 12, 2016 at 4:18 pm //


  7. @Geminidmn……You’re welcome. Keep us posted. Feel free to ask any follow up questions or other questions. And please let your friends know about us. Thanks! (Check out our e-reports on the seven most frequently asked questions.)

  8. geminidmn // July 19, 2016 at 2:15 pm //


  9. @Geminidmn……Glad to hear. Please do keep us posted. Enjoy.

  10. geminidmn // July 28, 2016 at 10:00 am //

    so the last time we were together, we now come to the part where he asks me what i want to do, we went out to eat then to the beach at night (again) and had a fun time, after we went back to my house and stayed up till 9am, at some point we were talking and i wasn’t really paying attention until he said however things pan out between us…, my mind stopped working after that, so does this mean hes thinking about how things will go and do i just sit back and wait or ask what he meant?

  11. @geminidmn……..Could you provide more detail? How did the conversation go down? In general, we’d follow his lead on this. A NOTE FOR THE FUTURE IF NEEDED: That said, there’s a timeline obviously. What that timeline is, is up to you of course? But waiting indefinitely for a guy to figure things out isn’t the best play, and will just bring you down emotionally.

  12. @All the Women out There…….We’d love to hear your thoughts on The Perfect Guy? Leave a comment, a description or respond to someone else’s comment. Let’s have a conversation.

  13. So, I recently started into a fwb relationship and simI large issue. Question is – is he really worried about me getting feelings or is there something going on?
    Background – Initially it took a lot of discussion before I agreed as I got out of a ltr a year ago. I’ve known my friend for 20 years, he was my little brother’s best friend growing up, and our moms and siblings are best friends. So I had a lot of reservations about this as we’ve been frinds so long and the family connection. But things have gone great. In general I’m a very blunt person with my friends, very caring, I like to joke around, flirt with guys I’ve had fwb with in the past and now, and just generally very friendly with people. We agreed no strings attached as neither of us are looking for a relationship. But he keeps saying “I don’t want either of us to get attached,” then now he’s worried about me catching feelings and not him because “he knows himself.” He was worried I’d get upset when he told me he’d slept with someone else and is nervous about our families finding out. But he’s fallen asleep at my house 3 times, leaving his truck in my drive way when both parents live within 2 blocks of me, and when I brought this up before he brushed it off. I don’t care he slept with someone else. He’s also suggested we go out for a few drinks together, has been over n just talked about past/present, and cuddles with me after sex.

  14. @Ryq2005….We’d listen to his words. He’s being very clear that he wants a no-strings attached relationship. Sleeping over doesn’t mean he’s catching feelings, or that he wants something more. If he did, he’d say it. What does your gut tell you?

  15. I’m so confused. I know I don’t want more than that and I’ve stated that, made it clear. We do text quite a bit back and forth even when he’s not coming over. He just makes me wonder if he’s projecting onto me. He apologizes when he can’t stay the night, hugs me goodbye, and just seems to be over thinking things. But has told me not to over think things when it first started. He says he doesn’t want our families to find out yet falls asleep n has the truck in my driveway overnight.

  16. And he’s made comments about his mom saying things about how he needs a girl like that, like me; and is hinting he should date me.

  17. @Rosalee…..What about asking him straight out? Maybe over coffee or lunch? When things are more casual. Would you be open to doing that? One way or another you need an answer. Seems to us, he’s the only one who can give you that.

  18. I actually tried. I asked straight out, no bs. All he said was “honestly I’m worried about you, I don’t worry about myself because I know myself.” Which I sled ecactly what he meant by that/how he knows that, to which he then dodges the question. I just worry he’s over thinning and going to ruin a good thing and long time friendship.

  19. Asked exactly*

  20. @Rosalee…..What he means is that he’s worried you’re catching feelings and are going to try to make this more than it is. A FWB arrangement. He doesn’t worry about himself because he knows exactly what it is. (That’s our two cents.) Good luck. Are you sure this is a good thing for you emotionally?

  21. Thanks for the insight. I’ve been very clear I don’t want anything more. I care about him a lot, we’ve known each other for 20 years, but I don’t want a relationship. I told him to stop over thinking this, stop over thinking me, and remember that even if we weren’t fwb my actions would be the same. Just like he would still be trying to protect me from certain things even if we’d never started this. Emotionally I don’t have the capacity for anything more. Things are too complicated for me, this is what works for me right now.

  22. @Rosalee……Okay. It sounds like you’re on the same page with him. So maybe it’s time for a quick discussion so you can both reassure one another that all is well and that you’re both happy enough with the arrangement. Sometimes when a relationship is not defined like a FWB, it requires even more communication not less. Nothing heavy, but just clear the air.

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