“Was it a Mistake to Sleep with Him on our First Date?”

I’m a 36-year-old professional woman, with my own place, a career, and graduate degree. I have no children, have never been married, and am pretty laid back. I tend to approach relationships at the speed of lightning, though, as in I get attached very quickly and I also am intimate with a man more quickly than most women I know.

Recently, I reconnected with an old friend online whom I haven’t seen in probably six years. He divorced two years ago and is the father of an adorable 7-year-old. Anyway, we met up for cocktails, one thing led to another, and we ended up having mind-blowing sex for the entire night until the sun came up. I completely did not expect it, but I don’t regret it either. Now comes the issues: we saw each other three times last week, went out one of those times for drinks and to hear music, but the rest of the time we hang out it’s only sex. I think I even made the GIGANTIC mistake of saying to him on one of our outings that he makes a perfect “friend with benefits.” Our sex can be very hot and intense, but also very romantic (we shower and he washed my hair, he kisses my forehead, he plays with my hair, etc.) and it is making me fall for him. Problem is, I’m terrified to have the “what are we?” conversation with him because I don’t want to lose him as: a) my sex buddy or b) my friend.

I have no idea what he wants out of our relationship, but I’m leaning towards just sex. He says things like “I’m not looking to remarry, but I don’t want to just hook up with someone and waste my time;” but I feel like he only hooks up with me, so am I a waste of his time? I feel like I deserve more but that I cheated myself out of it by sleeping with him so early on and making comments about being friends with benefits. Oh, we also text every day throughout the day and at night, so whatever it is I have going on with him it’s making it where I have no interest in pursuing anyone else because I’m wrapped up in him and wondering if we have a future together. I honestly don’t think he wants that, but I need an unbiased ear to give me the hard truth. — More than a Friend

You’re 36, not 16, and if you want to know if a guy “likes” you, the best way to find out isn’t by analyzing his behavior and the things he says — or worse, polling random people on the internet, which is kind of what you’re doing here — but having a real grownup conversation with him. I know you dread the “what are we?” talk, but what’s worse: the risk of rejection — because, come on, that’s what you’re really afraid of here, or the risk of losing this guy to someone who makes her intention much clearer than you have? If all you wanted was a “friend with benefits,” I doubt that as a sexually adventurous woman, you’d have much trouble finding that with someone else. So stop kidding yourself that you’re afraid you’ll lose that by opening up about how you really feel. What you truly want here is a relationship — an honest, open, adult relationship. And you aren’t going to get that by acting like a timid teenager who’s afraid to get her feelings hurt.

You wanna know where you stand with this guy? Sit him down and say, “You know how I said I thought you made a great “friend with benefits”? Well, I think I said that as a way to protect myself in case that was all you were interested in being. I wanted you to know I was open to that and OK with it. But as we spend more time together, I’m realizing that my feelings for you are developing into something a little deeper, and I’m wondering if yours are too.” Yes, you’ll be putting yourself on the line by asking this. You will risk having your ego and your feelings hurt. But if you don’t find out now where you stand, and you continue sleeping with this man you’ve got feelings for, and you continue analyzing his behavior, looking for signs that he has feelings for you, all the while shutting out any other potential mate because you’re solely focused on this one man, then he isn’t the only person you’ll be screwing in the long run. You run the risk of being deeply hurt if/when this FWB thing runs its course and he moves on to a woman who has made herself open — and yes, vulnerable — to him in more ways than one. If you don’t want to lose this man, you have to open up. And if you can’t do that, then you aren’t ready to be in a mature relationship, end of story.

*If you have a relationship/dating question I can help answer, send me your letters at wendy@dearwendy.com and be sure to follow me on Twitter and ‘like’ me on Facebook.


  1. I have nothing to add – perfect advice. You have to ask him LW. IF what you want is a long term relationship then in the future you should let the feelings develop before the sex – that way things don’t get so muddled up as they are now. Some people go on to have great relationships, even marriages, after sex on the first date but most don’t. Keep that in mind if what you are looking for is a relationship/marriage.

  2. Avatar photo Addie Pray says:

    Pretty please do what Wendy says TONIGHT and update us TOMORROW. … This letter could have been written by me. I wish I had had the guts to say, “You know how I said I thought you made a great “friend with benefits”? Well, I think I said that as a way to protect myself in case that was all your were interested in being. I wanted you to know I was open to that and OK with it. But as we spend more time together, I’m realizing that my feelings for you are developing into something a little deeper, and I’m wondering if yours are too” to a few guys over the years.

  3. Yeah, same here. It seems silly that you would prefer the risk of getting hurt down the line by continuing to invest your time, energy, and emotions on this guy and not just find out now where this may or may not be headed. I think we are all a little susceptible to wanting to “be in the moment” and ignore red flags. Trust me when I say you’ll kick yourself later if you don’t get this out in the open now. Who knows – you may be surprised at his reaction!

    1. Will.i.am says:

      It’s either to live behind the fascade and build a “relationship” in your mind, then lose the sex and the guy all together. Same works for men sleeping with women. Like the old saying goes, something is better than nothing.

  4. Judging from you’ve written LW, I’d guess he’s looking for some kind of relationship but just doesn’t want to get serious TOO quickly. I’m basing this theory on his whole “not looking to remarry, but I don’t want to just hook up with someone and waste my time” thing. If just hooking up=a waste of time, then it seems he’s looking for more?

    However, like Wendy said– TALK TO HIM. You are driving yourself crazy by analyzing the way he touches your hair, wondering if you slept with him “too soon”, & regretting your flippant FWB comment. All this head space you’re devoting to figuring shit out really isn’t going to help very much, unless you’re secretly kind of reveling in this “crush” stage where every little thing could possibly mean something? (I’ve been there, so no worries…)

    1. Oh god… I totally revel in the “crush” stage. I’m, like, 12 when I like a guy.

      Oh, but also – WWS. I had an answer similar to hers in my head before I read her actual answer and then I felt really proud of myself. But Wendy’s example of what to actually say to him is wayyyy better than anything I would have come up with on my own. I think I’ve actually said to someone, “Hey is this just sex to you, or do you actually want to date me?” It’s the same idea, but maybe a little too blunt, haha.

  5. WWS! Times a billion.

    This statement by the LW . . .

    Problem is, I’m terrified to have the “what are we?” conversation with him because I don’t want to lose him as: a) my sex buddy or b) my friend.

    . . . Is where single women get in trouble. The reason being is that LW, you obviously want to be more than fwb’s or friends. By continuing on this path – the path where you aren’t honest about your feelings to even yourself – you are going to start to feel really shitty. Trust me. I know. It took two years of therapy to kind of get it and I still have trouble.

    Talk to him already. It’s better to know his thoughts now than to sit and worry and wonder and second guess everything.

    1. spark_plug says:

      I just reread the letter – she just “recently” reconnected with him after 6 years? Really, you hang out with a guy three or four times weeks max (two of those times just banging) and now he’s a really good and trustworthy friend that’s really worth holding on to and has your best interest in mind? Really?

      I have a friend who had a rebound with a douchebag after her relationship ended. Even though he’s a pompous ass, she keeps talking to him because “he’s really smart and a good friend”.

      Having two intoxicated conversations with someone and sex afterwards does not make them your friend.

      1. I think she meant they were already old friends, not that they’ve become friends in that short time.

  6. Skyblossom says:

    I’m amazed that a successful 36 year-old woman hasn’t yet learned to speak in a relationship. I’m thinking of my daughter and hoping that I’m teaching her how to speak up in a relationship. She’s 12 so not in a relationship but I hope she ends up with the skills she needs.

    Speaking to a partner is not that different from speaking up at work. The first time is the most difficult and as you gain experience asking questions and speaking from the heart you find that it is easier than you imagined. You may get the answer you want and if you don’t you’ll at least have learned how to take the first step in talking about a relationship and what you want.

  7. was it a mistake to sleep with him on the first date? no.

    that really wasnt your question, though, was it?

    is it a mistake to keep all your feelings to yourself, pretty much lie to yourself about what you feel, and act like a 16 year old regarding every action and inaction he takes? yes. that is a mistake.

  8. At his current point it seems he doesn’t want to think about marriage, but is open to a committed relationship. That’s how I read this situation.

    Did you stop going out and doing things when you “accidentally” mentioned the FWB situation? Could be he followed your lead on that comment…

    WWS. FTW.

  9. laxhaxtax says:

    WOW!!!! It sounds like you and this guy connected pretty deeply. Don’t know many women who can say their men wash their hair or have sex all night long. Pretty darn intense. If you know that he has moved easily from one relationship to the next then he has his game on just right. If, on the other hand, this is not his usual MO then he may be feeling what you are. He has been burned once by marriage so he was upfront about not wanting that right now but that does not mean you and he can’t make a relationship. If you know him as well as it sounds you know whether or not he is a player. If not, then full steam ahead. I had that reaction to my husband and we have been married many years. Only man I ever dated whose touch was electric. I say go for it but be up front. Just don’t scare him off hovering.

  10. My current boyfriend and I were friends for about 4 years. One night we ended up hooking up (we didn’t sleep together). After that he started texting me every day and telling me he wanted to come visit me (we live in the same state but about 5 hrs apart). After a little over a week of this I started to get antsy about where things were going. So one day I called him up and basically said “I’m not interested in a penpal so this flirty texting and occasional hooking up thing that we’re doing now has to stop. If you want to actually date than let me know but if not I’m done with this.” His response: “I thought we were dating…” We’ve been together ever since. Basically what I’m saying is suck it up and talk to this guy. You never know what he’s going to say and it’s better to know now than to keep obsessing about it.

  11. laxhaxtax says:

    Also, I see in your letter a mild apology for having sex early after meeting a guy. For crying out loud. Women like sex. Why can’t we have it without feeling cheap or dirty. If you have sex on the first date so what. If the guy thinks you are a slut then so is he. I am so tired of this double standard.

  12. lemongrass says:

    You can still have a relationship after sex on the first date. My husband and I sure did. BUT you can’t have a relationship without communication and that is what you really need to do.

    1. the other guy says:

      And did you define your relationship as ‘FWB’ at this stage?

      1. lemongrass says:

        Nope. We talked about it shortly after and were both ready for an adult relationship.

      2. Just so I understand:
        1. within a reasonable time frame after sexual intercourse (i.e. not still sweaty and glowing but while the memory was fresh) you spoke actual words in an effort to communicate with someone you had previously felt fine inserting body parts into you?
        2. this effort to communicate included expressing yourself, including real thoughts and emotions??
        3. and your future-husband reciprocated by both listening and expressing his thoughts and emotions???
        4. this “communication” resulted in 2 consenting adults mutually agreeing on how to move forward in a relationship, which may or may not include further emotional and physical intimacy!?!

        I CALL SHENANIGANS! :)))

      3. lemongrass says:

        Believe it or not, this type of behaviour has led to 4 1/2 years together, home ownership, marriage and pregnancy. We must spread the word to stop this right now. Especially since the most painful part in our time together is right now, in my nipples, from this pregnancy.

  13. the other guy says:

    Seriously after a week you want to ask a guy ‘what are we’?

    Guys are simple creatures and most just of drift into long term relationships. Ask them up front are they ready for some sort of long term relationship and they will run.

    You have already set the terms of your relationship, namely ‘FWB’, that was a massive mistake actually stating it. As we say in business, put this down into the ‘lessons learnt’, don’t do that in future unless that is what you really want.

    1. lemongrass says:

      I think if a guy runs when you ask him what he’s looking for then you got the answer you were looking for.

  14. SweetPeaG says:

    I feel like this whole friends with benefits trend may be doing a slight disservice to single people. Look, I know that people can successfully pull it off. More power to you. I am not trying to say casual sex is wrong or anything. But, there is a downside. The true con to this whole way of doing things is that so many are left with feeling that this sort of relationship has to be something they are cool with. Women go out of their way to prove they are not be that clingy, crazy girl who wants to “tie a man down”! They have trouble being honest with what they want because God forbid they admit to wanting something more. That would be SO uncool if a woman actually wants to spend time with a guy she likes outside of the bedroom.

    Like I said… friends with benefits does work for some. And if you like it, I think that is really good for you! Really! But, if you don’t like it… grow a pair… and be honest. I have done just that in my single days. I have gone a step too far with a man (like our LW) and then realized that I was becoming a FWB. So, I told him “Hey, I am looking for something more than this. I don’t want to continue doing this this way.” It was hard to say, but I did. I acutally got the response of “You’re being so negative. We’re just having fun”… and got my answer. It sucked, but I felt so much happier in the long run- I knew where I stood. And really- nothing is better than getting to have sex with someone who also thinks I’m funny, wants to hold my hand when I’m sad, will listen to me complain after a hard day, and is proud to have me by his side.

    So yea- totally do what Wendy says and be honest! It’s true- it will set you free 🙂

    1. i really hate that divide between men and women… men dont ever want to be tied down (ugh i hate that phrase anyway), all women want is to be tie a man down, all men will run away at the first hint of a commitment, women are ‘crazy’/whatever for wanting commitment, the women who can do FWB are ‘cool’.. i just hate all of it.

      take it a step further, and i hate the commitment jokes around weddings. like the cake toppers with the guy in a ball and chain, or the one where he is trying to run away and the bride has him by the neck of his jacket.. the “game over” stuff.. and, i actually saw once a little flower girl with a sign that said “this is your last chance to run, daddy”. DADDY. it was her father and presumable her mother getting married, and she was carrying that sign.


      the whole thing just makes me sad.

      1. Preach! 😉

      2. lemongrass says:


      3. That is disturbing!!! Gross!

      4. quixoticbeatnik says:

        This reminds me – I was watching Bridezillas the other day and I was absolutely appalled by all of the brides. One bride even said in her vows that “When I first met you and looked into your eyes…I knew you were a one night stand. I’m surprised we made it this far!” Appalling. Tacky. MY GOD. She was a real piece of work. She only gave a fuck about herself…luckily the groom came to his senses after they married and she threw his dad out of the reception….and he dumped her. Of course, she didn’t think it was her fault. Oof.

      5. Moneypenny says:

        Yes! Could not agree more with this. And that sign sounds really tacky.

      6. What’s funny to me is, when I was engaged (long engagement – 3 years, because I was in college), I felt shocked! horrified! appalled! by negative marriage humor. My fiance’s brother got married before we did and I would hear him and his wife joke about who would out-survive the other, jokes about killing each other and inheriting each other’s stuff, etc. I couldn’t believe it! Why would people talk about marriage so flippantly, so negatively, like it was a burden or an open wound?

        Then, within the first year or two of being married, I found myself doing it too! Not jokes about killing each other, but for example: My best friend’s boyfriend treasures her and treats her very well, and they’re often lovey-dovey in public or I’ll overhear him say something super-sweet to her, and, can’t help it, “Just wait until you’re married, you won’t hear those sappy sentimental sweet-nothings for much longer.” Always in a joking way, not a threatening way, and no one takes offense – in fact, I’m pretty sure her BF will still be sappy-lovey-dovey when they’re married, he’s just that kind of guy.

        The ball-and-chain, “run away while you still can” stuff does still bug me, though. If my hubby and I ever use that language it’s completely jokingly, same as we might say “y’all” or “ain’t” to make a particular point but never in normal speech.

      7. But, I think making those kinds of comments gives the impression that it’s ok NOT to make those super-sweet comments when you’re married. Why do people stop doing the loving things they did when they were dating? I’ve been married for 2.5 years, and we still act lovey-dovey and make sweet comments to each other. I hope we never stop. And I would never want to give the message that it’s expected that it does stop.

      8. I don’t think it implies that it’s not OK, but that it’s normal for lovey-doveyness to peter off after marriage and/or living together.

        And I admit my own relationship trajectory isn’t standard. We’ve been together over 10 years, since we were freshmen in high school, and coming up on our 3rd wedding anniversary. I think we each sort of lost our “sweet tooth” for lovey-dovey stuff in those first seven years. Like, if you eat chocolate chip pancakes for breakfast every morning for seven years, they sort of lose their appeal and become ho-hum, nothing to get excited about, nothing you make an effort for.

        Not to say we’re never lovey-dovey. We have our moments. But in comparison to my best friend and her BF, we almost look frigid. He’s the type to hang on her every word, do any favor she asks, bend over backwards to make her happy. And I look at that and am happy for them, but I also can’t help but laugh, because I can remember a time (wayyy long ago) that Mr. KKZ was that way with me, and now we both bitch at each other, tease each other, call each other out, etc. Not ALWAYS, obviously, this is far from a loveless marriage – but like “Hey, can you help me find my hat?” — “Again? You are always forgetting where you put it. If you put it in the same place every time, this wouldn’t happen.” (Not… “Sure, sweetie!”)

        Get what I’m saying?

      9. I should include that I’m not upset about this whatsoever. It works for us. Probably 80% of the time we are pragmatic and non-romantic with each other (hey, shit’s gotta get done, we have a house to run and careers to maintain and a dog to care for), and 20% in lovey-dovey mode, giving backrubs, cuddling on the couch, lots of kisses and I-love-yous. I can’t count on him to hang on my every word, but I don’t think I’d really want him to. At this point it would be weird.

      10. lemongrass says:

        I’ve been married for a year and still say sweet things, I hope we always do. My husband also says that I’m “with him for his hundred’s” and I tell him not to get hurt, we don’t have life insurance yet! Some people seem to wince at that joke but he knows how much I love him. But really, we do need life insurance.

      11. I find it admirable you presumed it was his baby’s momma walking down the aisle 😉

    2. I wish I could like this 100 times.
      Women of the world: it is OK to be FWB but it is also OK to want more. Wanting a real relationship does not make you clingy or needy. It’s ok to want a guy to take you on dates, hold your had and ::gasp:: actually enjoy talking to you. Not everyone is cut out for FWB (more power to those who can do it) and its ok to tell a guy this. Better to be upfront with your wants and needs.

      1. Totally agree. It is perfectly okay and normal to want a relationship! I don’t know why there is such a perceived stigma on this subject, that otherwise capable and independent women (and men, let’s be fair) silence any mention of their needs in order to appear “cool” with “just having fun”. I think so many people do themselves a disservice by remaining in situations where their needs are not, and won’t be, met. If, after a decent interval of water-testing, your date/FWB/whatever does not want what you want – move on and find someone who does! So much grief could be saved.

    3. Well put SweetPeaG. It’s not that wanting a FWB situation is wrong, it’s just that it’s sad when people (men and women) really want more and pretend not to because wanting a relationship makes you “clingy” etc. It’s amazing how we can lie to ourselves, too, and convince ourselves that we only want so much, so as not to “scare” someone away. That’s been the best thing about getting older, for me. I’m not such a people pleaser and I can focus on what I want. If I “scare” you, then fuck off! I like relationships, and the right person for me will too.

  15. quixoticbeatnik says:

    The only thing you can do is talk to him – and the worst thing that can happen is that you lose him. I used to have a similar problem a couple of years ago, and I kept quiet for a long time….mostly because I was afraid of the answer. But eventually I got sick of wondering and just flat-out told him that I liked him, and that I thought he liked me too – SO what was he gonna do about it? Well, he did nothing. I wasted two and a half years on a guy that wasn’t ever my boyfriend. And we didn’t even hook up! The most we ever did was make out, one time. It was really pathetic actually. The most annoying part is that he still pops up from time to time, wanting to ‘chat’. I try to ignore him as much as I can, but it’s hard because we were such good friends back in the day.

    Now I have my lovely boyfriend who I’ve been dating for the past couple of years. I’ve always been pretty honest with him about how I feel. Just tell him.

  16. You already know that you have issues with getting close too fast, so nip this in the bud! Talk to him and let him know that you love sleeping with him, but that you aren’t looking for a friends with benefits situation. So what you said it once–one time I said I wanted to be a teacher, and an illustrator, and once I hated tomatoes and now I love them. Who cares? People change their minds.

    You are regularly sleeping with, hanging out with and texting this person. ASK! Otherwise you are setting yourself up for a scenario you already know you have problem with.

    If he says he just wants sex, MOA; you deserve what you want but you need to be bold enough to take it. I don’t feel there is anything wrong with having sex–you guys are adults. But don’t get it tangled, just have the conversation!

  17. So how come one of these times he’s talked about not wasting time you haven’t just asked “is that this is – wasting time?” It would have been a natural flow to the conversation and you could have learned what you wanted to know and shared with him that you would like to move into relationship territory. But you don’t really want to know what he thinks do you? Because what if it’s not the answer you want. Yes that would sting, but I think it will hurt a lot more if this continues and he cuts off what he thinks is a FWB situation because he’s met someone he wants to have a relationship with. So do you want your pain now or later? Or maybe, if you pull yourself together and talk to him like a mature adult, you’ll find out he wants a relationship with you. I think you should find out before you drive yourself over the edge trying to read into every. little. thing. he says or does.

  18. spark_plug says:

    The LW reminds of me the LW from last week that hadn’t met her boyfriend’s family after dating for 9 months. Another self-proclaimed successful woman who has so little control over her relationships.

    Three things stood out to me in this letter:

    1. That the LW jumps into bed quickly and openly expresses her interest in sex, even though it might end up working against her in the future. I’m not going to judge on when and how soon, but I do know that some women use sexual behavior as a defense mechanism. Why did she tell the guy that he just wanted FWB, was it because a) that’s what she truly wanted at the time, b) she has a tendency to blurt/do things out in the moment while not thinking of their impact on the future or c) it’s what she thought he wanted to hear. Judging from her tone on him for the rest of the letter, I’m inclined to think its (c) and if so, this LW is not operating from a very healthy place. If its (b) then the LW might need to learn some self restraint or to think about the future implications of her actions more. And if its (a) and the LW is really empowered to express herself then why limit to the sexual relationships as well? You can take the same control in your non-sexual interactions as well.

    2. What is up with women being so desperate to hold on to a guy they are willing to sacrifice their own wants and needs? Yes, conflict is scary when you like someone and there’s a BIG chance that he might say – sorry, just want sex – which would really hurt and suck for the LW. But doesn’t it suck to be hooking up with someone not knowing where you stand, being able to express yourself or not being sure that they even care about you? Is keeping an orgasm or someone’s attention really worth your anxiety (and if you’re writing in a letter you’re anxious!) and sacrificing your wants? Especially at 36? Is this an isolated incident or does it happen in your other relationships and interactions?

    3. LW – what do you want? Is it just to keep having sex with guys? Is it a relationship? Marriage? Decide what you want and then act accordingly. I’m not saying that relationship cannot happen out of one night stands as they do all the time but more often then not they don’t (please don’t flame me!) And even if you’re not sure what you want… take a few days or dates, get to know the guy and then decide how to proceed – especially if you know that if you develop feelings for him you will start to feel very powerless and afraid to express yourself.

    1. SweetPeaG says:

      Decide what you want and then act accordingly…

      Yes! This could be a one sentence answer to so many of the LWs.

  19. Are you a hip chick who’s got it all together and can enjoy a hot fling or are you a 13 year old passing notes in class to find out if a guy likes you or not?
    So far you’ve rushed in to sleep with the guy, blabbed that FWB is a-okay, read feelings into kisses in the shower, and now want to have the “what are we talk” all in the space of whatever time frame “recently” is?
    I suggest you give yourself a time-out. Tell Mr. Hot Pants that you’ve got a heavy week ahead and will likely be away from your (over-used) qwerty keyboard for the duration and just chill out. Give yourself some time to think about who you really are, what you really want, and whether it is oxytocin talking or whether there might be something worthwhile there. Create a space from all the textin’ and sexin’, do things with other people and get some perspective back. Give the guy a chance to miss you and observe what he does.

    1. SweetPeaG says:

      Agreed. And enjoyed your use of “Mr. Hot Pants”!

  20. wow…i could have written this letter! LW if you want another perspective i have one word for you…patience! keep seeing the guy and see how the relationship develops…having a conversation with someone does not guarantee that one or both of you won’t be feeling the same way in a month…two months or more time down the road…it takes time to develop a relationship…and i don’t think becoming physical early on will negatively impact the relationship (he was there too!)…i’ve been in relationships where we had the “what are we talk” early on and then two months later broke up…i think actions speak louder than words…so my advice…be patient and see how it plays out

  21. LW, definitely do what Wendy said, that’s great advice!

    And I will add, that if sleeping with someone right away makes you this uncomfortable that it would cause you to continuously doubt yourself and question whether it was the right thing, maybe you would be better off waiting? All power to people who do it right away because they want to and overall it is worth it to them, but not everyone is built like that and that’s ok.

  22. tbrucemom says:

    Since they had sex from the get go I don’t think it’s a stretch to think that’s what the relationship is about at least at the beginning. It does sound like there is more going on than just sex so I’d tell the LW to do exactly what Wendy said and go for it. He’s only been divorced 2 years and has a young child so it’s understandable that he’d want to take it slow, but I think it’s better to know now whether or not he’s seeing anyone else, if he’s interested in a relationship now or in the future, etc. I think as women we tend to overanalyze everything where men usually don’t. Even though the LW is 36, I think deep down we all still think like we’re 16 when it comes to “boys”, lol, and I say this as a 51 year old!

  23. 6napkinburger says:

    Maybe I missed something in the timeline, but it seems that this is the very beginning of your sexual relationship with him, not a dragged on version of it. I think I would say that you should relax a bit and see where it goes, keeping in mind that you are entitled to want what you want and not to do what you don’t want to do.

    What I mean by that is, if you’ve been sleeping together for a week, don’t have a convo about “where this is going.” Just let it develop. If you want to go out on dates, suggest dates and (nicely, but firmly) reject just sleepovers or late night requests. Show, don’t tell. 3 in one week with a date at the very beginning does not sound like a FWB, it sounds like you’re in the passionate beginning. Try your best not to freak out and just to continue to discover if you like being with him. If you don’t let him “use you as only a FWB” (Which I don’t think he’s doing at all) he can’t and the relationship won’t develop like that. It isn’t just his call how this relationship develops; its yours too. Shape it to get what you want and don’t let it go a place you don’t want.

    Plus, if you’re having sex 3 times a week, chances are he isn’t sleeping with someone else, so for right now, you don’t have to have the exclusivity talk quite yet (but of course practice safe sex). I’m not saying communication isn’t good or isn’t usually the best way. I’m just saying having the defining the relationship convo after a week might stiffle the natural progression of a great relationship because it requires identifying and labelling feelings that haven’t developed sufficiently. This sounds like an awesome situation — allow it to develop the way you want it to.

    1. 6napkinburger says:

      PS I hooked up with my (now ex) BF on the first date and slept with him the next night, and practically moved in the next weekend; we were together for 2 years. When it’s “right”, all rules go out the window and just don’t apply. Ask most of the happy couples you know — almost all of them broke some cardinal “rule” when they were courting.

      1. So true! Sometimes, as cliche as it sounds, when it’s right, it’s right and that’s really all you need to know.

    2. 6napkinburger says:

      Note: I didn’t see the line about not wanting to get married again. At some point, when its hypothetical, I would ask if he means right now or if he means ever. See how he responds. If you’re a marriage minded person and he is adamantly against marrying again, you might want to piece out now. (MOA) But if he just means that he’s not ready now etc., then proceed with my other advice.

  24. Avatar photo sobriquet says:

    I’ve been here before, in my early twenties, when I was very lonely. The guy fulfilled certain needs (physical, emotional), but I knew deep down that he didn’t want a relationship. I never brought it up because I figured I’d rather feel slightly used and have him around than go back to being super lonely. Hindsight? It was not fucking worth it.

    I certainly hope you’re not in the same boat I was, LW, but it DOES sound like you’re in denial about your feelings. You’re repressing the thought of being in a relationship with him because you don’t want to go back to being alone (let’s face it, you don’t care about being friends with the guy). At age 36, however, you need to own up to your feelings and stop wasting your time with someone who isn’t giving you what you need. I’m not saying he doesn’t want to be more than FWB’s, but you have to talk to him about it. And if he doesn’t want anymore than that? I suggest you move along and find someone who does.

  25. Hello everyone, I am the LW! I can’t tell you how much I am enjoying and truly processing these comments and Wendy’s advice. It’s also fantastic how quickly she responded to my letter b/c I am STILL in this limbo with this guy. It has only been 3 weeks for those of you wondering, so it’s still very new, but I know i have to have the talk with him the next time I see him. I am already waist deep and don’t want to be in over my head. I do not know why I can read sound and mature advice and always take the immature route; but that is definitely something I have to work on. Pretty much what everyone has said is correct, I am very immature with relationships because I try to do what the guy wants and I try to preserve my own feelings, thereby masking them and creating this fantasy world where I pretend to be uninvoled when all I want to be is INVOLVED. I know what I have to do, and it’s been a real eye-opener to hear it from unbiased people. I truly appreciate it everyone! I’ll udpate you after the discussion…

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