Friends with Benefits

[simome05]

In June 2014, I started dating a guy and in October 2014 we ended it because I lived in MN and his new state of residence is unknown because he's a pilot. We started talking again and being flirty with each other. But, I wasn't sure if he had feelings for me again or something else. So, one night we were texting and I accidentally told him I had feelings for him and he reminded me why he can't be in a relationship right now. Which I totally understand and we decided to be friends and occasionally friends with benefits.

So, here's my question. Next week I'm in Fort Meyers florida for work and he's currently based their for the month of January. How do I bring up the subject of possibly getting together for a drink and cashing in some of those benefits. I'm not really a forward person, but he's definitely more forward with me and I like that. So, what's a good way of approaching this subject? I really like texting examples, too!!!!

Please help!!!

[Heather]

Is this really okay with you? I ask because you have sounded awfully hung up on this guy, and nothing close to casual, IMO. Casual sex -- which FWB often falls under when the people involved aren't coming into it as longtime friends -- can be a fine thing, but it doesn't tend to feel so great when you don't really want or feel casual. Sometimes, too, people who really want a different kind of relationship with someone offering only casual will say yes, figuring at least they get that and maybe it'll turn into that other kind of relationship, and that doesn't tend to net good results, either, most of the time.

If you have had a change of heart and do feel good about this, then really, all there is to do is ask him what you're asking about asking him. In other words, you call him and ask him out, a la "Hey, want to get together at <wherever> around <whatever time>?" or "Want to get together for a drink soon? If so, when works for you?"

[simome05]

I'm the one that suggested the casual sex. I had no plans on ever telling him, that I still had feelings for him. Because, I had decided after reflection that he's not in the position to give me what I'm looking for in relationship. But, I thought why not be friends and if he wanted to be friends with benefits.

[Heather]

So, you no longer have those same feelings, and what you want in a relationship from him has changed? If not, how do you feel about pursuing something that is not what you want, and being dishonest about your feelings while being sexually intimate with this person?

[simome05]

Yes, I know longer have feelings for him. I'm totally fine with being friends and friends with benefits. I reflected a lot about the situation and realized that we can't be in a relationship with each other, but we can be friends and friends sounds great to me.

[Heather]

Okie dokie. Just wanted to check because you'd been so hung up for so long, and was having such problems being honest and assertive with him in the past.

That said, if you're going to be friends who have sex, then the way to come at this stuff is the same way you talk to friends. In other words, you shouldn't have to be thinking very hard about how to do something like asking someone if they want to hang out. If it's casual...well, it's casual, and there just isn't any need to have to work so hard, if you know what I mean.

And if you still feel like you can't just comfortably interact, I'd say it might be time for another go-round with your thoughts and feelings about how maybe you and this guy, period, aren't such a great fit. When we are a good fit with someone, and this has gone on long enough for you to know, things will tend to feel pretty easy and comfortable, not chronically uncomfortable or unsure or like we have to do everything just-right all the time.

[Heather]

And if you haven't seen this, it may help you to think about and navigate this terrain: Casual...Cool? Making Choices About Casual Sex.

[simome05]

Thank you for your advise. I'm horrible at vocalizing my feelings about anything and I don't understand why? I've always been an over thinker when it comes to work and personal life. My friend keeps reminding me that it's actually not this difficult, your making it more difficult on yourself. Maybe it's because I havent been in very many relationships. I will definitely check out the casual... cool? page.

[Heather]

I guess I just wonder if with this guy, this is so much about you overthinking, or you mistaking overthinking for this just being way too hard.

Following all of the history, it just sounds like this guy hasn't been all that enthusiastic or responsive a lot of the time. A person can't develop any kind of relationship by themselves, after all, and when things are very one-sided, it is going to feel like a struggle, even without overthinking, because it is one. same goes with feeling able to express yourself and be honest about your feelings: when someone else is barely even interacting with you, and doesn't seem to want to share themselves, it's going to feel that way, and that's not about you doing anything wrong besides potentially just barking up the wrong tree in terms of pursuing someone who just doesn't seem very interested.

Truly, when it's right -- no matter what kind of relationship or interaction it is -- it doesn't feel like such a struggle (setting aside when someone has issues like social anxiety disorders or other things that make all socializing very hard for them). It feels pretty darn easy and comfortable. When it doesn't, that's most often a cue something just isn't right, or despite being attracted to someone, you just aren't connecting with each other. And, of course, when one person is massively hiding out in their feelings and the other just isn't really putting any energy into connecting with that person, you're not going to be able to connect, or at least not very well.

If this is stuff you just don't want to talk about here, btw, you don't have to. It's just that with such a long history here from you about this guy, and this never really seeming like it has ever felt right for you, and him pretty much only communicating clearly with you when he's telling you what he doesn't want with you, I felt like I needed to put some of this out there. You've invested a lot of time and energy with this person, far, far more than it seems like they have with you, and it'd just be a bummer if continuing to do this in any way is just you wasting that energy and time.

[simome05]

We were both very enthusiastic when we first started dating. He was so sweet and would text dorky things all the time. We always had a lot of fun and he always texted to make sure I go home safe and said that he would call me the next day. Then 6 weeks into dating he got sent to training and he said it will only be 4 weeks and the time will fly. I felt it was important during that time to let him initate any communication initiate during that time. Which he did a lot and we actually had a lot of fun. Then he came back for 2 days and we decided to take it to the next level. We both said we weren't seeing other people and decided to take it to the next level. When he left we decided to continue this new level when he got back. He was very honest about possible being for a month or longer. Then I became impatience and started listening to my friends bad advice. Then asked him if he wanted to continue this and thats when we ended things. I don't feel like it was one sided.

[Emma]

Some things that confused me in your reply are firstly "I felt it was important during that time to let him initiate any communication initiate during that time." Why is that? Do you feel weird or overbearing if you contact him or ask for what you want from him? Even in a "Friends With Benefits" relationship, comfort in open, honest, vulnerable communication is very important and it doesn't sound like you have that kind of relationship with this pilot.

Secondly you said you "started listening to my friends' bad advice." Was the advice that you should end things with him? It seems like your friends had a say in whether or not this relationship continued--is that something you're ok with?

[simome05]

I wanted to be respectful of his training. I know the hard process of pilot sim training. Once he initiated communication a couple of times I did feel comfortable texting him more. At the time we were dating and I was still seeing other people. I think being honest about anything sexual or relationship is just hard for me. I grew up in house sex and anything under that topic is never spoken of. My mother always grounded into our heads.." You don't do a thing until you got that ring." That was the only thing brought up about sex at my house growing up. I'm a very shy/ introvert and he has definitely brought me out of my shell. Which has been a wonderful thing. But I still get nervous when he texts me about naughty/ dirty things. Half the time I don't catch it. Lol! And same for him sometimes.

My friends kept telling me I was so boring in my texts and that I needed to step it up. My other friend kept pressuring me to ask him if he was my boyfriend or boy toy. Which I never did. I think I became frustrated and impatient because of that. My friends kept telling hi is he ever coming back? If I could go back, I definitely would've never listened to my friends. They made me impatient and turned me into a person that Im not. I think I went to them for advice because they've been in a lot of relationships and I havent.

[Heather]

Simome: I am so sorry, I did not mean to turn this into something where you feel like you have defend this, or yourself, in any way. I just felt some concern given the history you have posted here over many months, and wanted to check up on you around it. By all means, if you do not want or need that, we do not need to go there.

[simome05]

It's fine... And I totally see your concern. It does feel a lot better that I put my feelings on the table and he was so sweet with his explanation why we can't be together. I knew this would be a possibility when I started dating him. But, always hoped that it would work out. But I've moved on and will continue to date and hopefully meet the right guy. But in the mean time I guess it doesn't hurt to have. Right? And we do have a lot of fun together.

[Heather]

For sure, when any kind of sexual interaction or relationship feels like something you want and it makes you feel good physically and emotionally, it not only usually can't hurt, but can be something very positive. A sexual relationship being positive isn't really about what kind it is, and, in general, more casual, or non-romantic, or uncommitted sexual relationships or interactions are no less likely to be beneficial for people than the alternatives.

It's just a matter, in any given situation, for any given person, of considering and exploring the specific one at hand and finding out if it's something that's a good fit for you.

[simome05]

And I totally agree. Might as well have fun until I meet the right guy. So here's a question about communicating when your friends with benefits. Since he's my friend, guess I just treat a text to him like a text to any friend. Right? But knowing with him it could always end up more sexual. Which I don't mind one bit. Also since I spilled the beans I've been very cautious about what I say. Can I say to him.... What? No more dirty/naughty texts. Or is that to much? I honestly don't a have a clue. Is their a website out their to navigate texting with a guy your fwb with.? Do I bring up when should we use our benefits? The great thing about him is he makes me feel comfortable about my body and it makes me feel good about myself. It will probably take me awhile to feel that comfort in a new dating situation. So in the mean time, why not have some fun?

[Heather]

Again, I really think that this is something where you have to feel like you can just say what you want to say. And where no one else can tell you what the 'right" thing is to say, because the only thing that makes these things right is that you want to say them and that they feel right for you -- only you can know that.

I hear you saying that this is something where you just want to throw some caution to the mind and try it out. So, if I have that right, how about...well, doing that with this stuff that really puts you at risk of nothing besides potential disappointment? You don't really risk anything besides that here by just saying to him what you want to say in the ways that feel right to you.

And if you aren't sure what those are, and feel like you need someone else to literally give you directions step by step (which you are not going to find, because this is YOUR relationship, and no one else can be you and this guy except you and this guy, I'd say that is a cue you just need to work more on just trying things, and seeing how they go and how you feel about them, or looking more to your own wants and feelings here and letting those be your guide.

Once more, a lot of this is really about how comfortable you truly feel here, and with this situation. If it's not comfortable enough to just text what you want to say when you want to say it, then I think it's sound to try and figure out why, rather than trying to find someone else to write your script for you, you know? And I can't know the whys here, only you can.

[simome05]

I know... I just don't want him to think I'm a slut or something with sending a text like that. But I think he knows I'm not. It's just me beIng my normal overthinking self. But does that text sound sluty? "What? No more dirty/flirty texts? Lol! "

[Heather]

You know, "slut" and "slutty" is not a framework we use around here or that tends to be useful. Usually all 'slut" or "slutty" means is that someone thinking that about someone else feels that person isn't being sexual in a way they approve of, or, if someone is thinking about that about themselves, that they worry their own actions or choices may not be a fit with their own sexual values. It's all very arbitrary, and mostly about words just meant to make people feel shame. That terminology and kind of framework generally isn't helpful when it comes to anyone just sorting out what they want sexually and what they feel good about when it comes to their choices and interactions.

But I'll be plain: this is about a casual relationship that would be primarily about sex. So, if you feel like he is asking for that, but worry that somehow you going along with that and communicating with him sexually wouldn't be something he wanted or accepted, you two clearly need to talk about this together. I mean, if you don't feel like you can ask for or suggest sexual things in an expressly sexual relationship...well, that's kind of like agreeing to go to a restaurant when you're not sure it's okay for you to go ahead and put an order in for food, you know?

Or, again, maybe you need to rethink if this is something you really want. After all, something like this is all about just being casually sexual with someone else, and that includes them thinking about sex with you casually. If that bothers you, or you're worried about them thinking about you that way, then you probably don't want to enter into a kind of relationship, like this, where both people are basically agreeing to think of each other that way.

But really, in this conversation so far, I hear you voicing a lot of issues with listening too much to others input about your choices and actions. So, it seems to me continuing to seek that out, rather than going with your own gut and exploring on your own, leading with what YOU want, only sets you up for more of that. If this is just about having fun, truly, then it should be something that can be fun and light, including in something as small and minor as text messages between casual partners.

[Heather]

Simome, as I was walking out the door from work, something else struck me about some of this I figured I'd toss your way in case it's helpful.

Things-for-fun, fun things, are supposed to be fun throughout, not just fun some of the time, or for part of them. So, if this is about having fun, the whole bit really should feel fun, including things like sending a flirty -- or more than flirty, an outrightly sexually suggestive -- text or message. Having fun with something like this means letting yourself have fun with this part, too, and really focusing on that and what feels good -- and fun! -- for you.

So, again, if even right at the start, something as minor and small as sending a text doesn't feel fun, that's probably because this really isn't what you want or a good fit for you, and the rest likely won't be much fun either. But if you can just lead with what does feel fun for you, including things like texts, and feel comfortable having that kind of fun, the rest not only will likely be fun, it'll be a lot more likely to be, and a lot more likely to just plain be okay with you, and a good fit for you, than if this feels like something you can't let yourself go pretty freely with, and feel like you have to labor over or do "perfect."

Long story short: if and when it's about fun, it should be fun, start to finish. If it feels stressful, uncomfortable or hard for you right from the start, and like something you can't let yourself be even just a little bit free with, especially with stuff that is just, in the grand scheme of things, nothing (like a single text message)? Probably that's because this kind of setup just is NOT fun or right for you. It's not for everyone, or for everyone every time, or in every situation.

[simome05]

Update: just got back from Florida and seeing the pilot. We talked on the phone a week before going down. It was so nice and funny. I told him I was staying in fort Meyers and he said why don't you just stay at my hotel. So after some thought, I agreed and stayed with him. We had a lot of fun and did explore our friends with benefits relationship. The only thing that sucked was he was sick . I think mostly warn down from work, but we still had a great time. FWB is alittle different then I thought it would be. We went out to dinners , comedy shows and movies. I really wanted sex and we did have fun but the best part was just cuddling with him on the last night. It was the perfect way to end the trip.