Dear Wendy
Dear Wendy

“I’ve Fallen for my FWB’s Best Friend!”

“Tim” and “Seamus,” my recent FWB, have been best friends since high school. They are now in their late twenties and have been living together for six years. I met Seamus about two years ago in a community that we both belong to and we have become good friends. About six months ago, Seamus and I confessed our long-held, poorly-concealed attraction to each other and began a friends-with-benefits (FWB) kind of situation. Neither of us wanted to date; I’d just gotten out of a year-long relationship, and he was at a bit of a transitional point in his career and life.

In the beginning of our friendship, Seamus and I started having brunches and games nights with Tim and his then-girlfriend, and Tim and I hit it off right away. The first time Tim and I hung out on our own, we talked for hours, wandered around our city, perused comic books and ate fancy grilled cheese. We became fast friends and I had a fleeting thought that he was perfect for me, but I knew he had a girlfriend. Shortly after Seamus and I started sleeping together, Tim and his girlfriend broke up.

Since then, Seamus and I stopped seeing each/sleeping together/whatever we were doing. My feelings changed, or his did, or maybe they both did. I wanted more, he started pushing me away, and, in the distance, I realized how poorly-matched we really are. We remain friends; we both love our community and have fun hanging out within it, with the occasional coffee here and there.

About two months ago, Tim started dating someone new. It was fast and intense, and Seamus and I watched with our eyebrows just a little raised. Tim says he fell for her right away, but he has explained to me that he feels a little stuck. He doesn’t know what to do now, he says. It all happened so fast, and now he doesn’t know where to go from here. It has been clear from the very beginning that Tim has had feelings for me. Before Seamus and I ever became a thing, Seamus told me that, if it ever became relevant, he would be uncomfortable with Tim and me dating. I know he has told Tim the same thing. I also know that this still holds true. However, it has now become an obstacle.

Since I am no longer with Seamus, Tim has become more vocal about his feelings for me, feelings he apparently still has. We have always had a little bit of a flirty banter going on but, at least on my end, it has never had true sincerity behind it. Now, though, I think back to how he’s always treated me. I think back to that first time we hung out, which, in hindsight, looks like a date. I think about how much I’ve grown to care about this man and I realize I care about him more than the friend I’ve always called him.

This is not simple. I know Tim cares about his girlfriend, and I know he is happy with her, although he has told me that he knows he could be happier. I know that, against all logic, Seamus still feels possessive of me. I know this has “drama” written all over it. But I can’t let it go. I know you’re going to say I should. I know I should. It’s not like I’m going to put my romantic life on hold for a man who is currently unavailable, and nothing has or will happen between us so long as he remains unavailable. But, if he became single and Seamus got over himself, I don’t see what else would hold us back.

I can’t stop thinking about it. I feel guilty for even considering it. Maybe I’ve answered my own question. I’m not even sure what my question is. What do you think? — Double Trouble

What I think is that Tim has much, much more to risk by dating you and disappointing/hurting Seamus than you do. You might lose an acquaintance you have occasional coffee with. Maybe things would be awkward in your mutual community and you might be forced to find a new group to hang out with. Big deal. Tim, on the other hand, would risk losing his best friend. If that were a risk he was really willing to take — if his feelings for you were strong enough to potentially throw away his friendship with Seamus — he probably would have pursued you in the window of time between you ending your fling with Seamus and Tim starting a relationship with his new girlfriend.

Sure, you could argue that the risk might be worth taking for Tim if he had confirmation from you that his advances would be welcome. Maybe if HE didn’t have to be the pursuer, the risk of losing Seamus’ friendship would be even easier to take. But I still say that if Tim felt strongly enough for you, he would have figured out a way by now to act on those feelings. I also think that, if you were to pursue him, either now while he’s with his girlfriend or in the future if they break up, and he was receptive, there’s a good chance he would resent you if being with you cost him his closest friendship.

I’d recommend you hold off on doing anything. Let nature take its course. If things don’t work out between Tim and his current girlfriend and you’re still single and enough time has passed since your FWB situation with Seamus, then maybe the current will pull you two together without much effort on your part. But if it doesn’t go that way, just let it be. There are enough men out there that you don’t have to pursue someone who is unavailable to you in multiple ways, however perfect you might think he is for you.


You can follow me on Facebook here and sign up for my weekly newsletter here.

If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.

43 comments… add one
  • kerrycontrary May 20, 2013, 3:01 pm

    WWS. Just let nature takes it course. Plus, I think it’s pretty shitty of Tim to stay with his current girlfriend while hitting on/pursuing you. And remember that your life is not a romantic comedy where you end up with your former fling’s best friend and everyone is so happy for you. What you are considering (breaking up a friendship) has possibilities of doing real damage to people and their relationships.

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  • landygirl May 20, 2013, 3:11 pm

    Are these the only two guys left on the planet? Find a new guy wholly unrelated to your group and be just friends with both of these guys. Problem solved.

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  • Fabelle May 20, 2013, 3:18 pm

    I totally agree with Wendy that Tim would’ve pursued you already if his feelings were that strong. If I’m reading this letter correctly, he was single during the same time you & Seamus weren’t sleeping together anymore—right? So that would’ve been the perfect opportunity.

    So I’m gathering that Tim’s friendship is more important than whatever crush-like feelings he has for you, LW. (I do agree that Seamus should get over himself, though. Who knows, maybe he will one day. In the meantime, continue to NOT let this prevent you from dating other people.)

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  • ebstarr May 20, 2013, 3:28 pm

    Idk, I think she should ask him out when he’s single if she wants. Seamus SHOULD get over himself. The LW should take a stab at figuring out if this is the love of her life. (If he says no just because of Seamus, then Wendy’s right, he’s probably not the love of her life.)

    The “fancy grilled cheese” thing cracked me up. It’s just so urban hipster. We’re meant for each other… because we both like grilled aged manchego on rye with organic bacon! (I say that with love – I’m obsessed with a fancy mac’n’cheese place in my city myself. Specifically the brie-fig-goat-cheese concoction they serve there. Any guy who feeds me that has a shot at Love-of-Life status.)

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    • honeybeenicki May 20, 2013, 3:40 pm

      There was a restaurant on Shark Tank on Friday that is all grilled cheese. I can’t remember the name of it yet, but if they franchise anywhere within 200 miles of me, I fully intend to check it out. Mostly because they have a grilled cheese made with a glazed donut. And that has to be a) delicious and b) extremely healthy.

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      • honeybeenicki May 20, 2013, 3:43 pm

        It’s called Tom + Chee.

      • rachel May 20, 2013, 3:47 pm

        We don’t have that restaurant, but there is a grilled cheese place in Milwaukee I’ve been meaning to try.

      • honeybeenicki May 20, 2013, 4:10 pm

        I should drive down there some time and check it out. In my head Milwaukee always seems so far away when in reality I can be there in an hour and a half.

      • ebstarr May 20, 2013, 3:48 pm

        omg I must have that.

  • Lily in NYC May 20, 2013, 3:36 pm

    You were never serious enough with Seamus for him to say you “can’t” date one of his friends. If Tim is into it and isn’t worried about Seamus getting upset, then I say go for it. But this is really not quite the dramatic situation you make it out to be. Either just let things be or don’t. But don’t keep dwelling on this and if you are analyzing every little detail with your friends, then take a step back and breathe. However, my gut is telling me that Tim is going to live by the “bro code” and is not going to express interest in you. And please take anything he says about his girlfriend with a grain of salt – he is probably just trying to keep you on the hook a bit because he likes the banter you two have. But the fact that he talks about his girlfriend with you at all would be a dealbreaker for me. I can’t stand when women/men discuss their relationships with people they flirt with. It’s so disrespectful to his GF.

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    • Copa May 20, 2013, 4:38 pm

      I wholeheartedly agree with the last three sentences. That was one of those details that just made me wonder why you’d want to date him in the first place. I get that it’s flattering to think that this (taken) guy is telling you he’s unhappy with his curent girlfriend, and that he’d be *so* much happier with you, and that he’s OBVIOUSLY telling yout his for a reason — but it’s tacky and speaks volumes of his character to me.

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      • kerrycontrary May 20, 2013, 4:46 pm


      • Lily in NYC May 20, 2013, 4:52 pm

        And you just know he’s probably bad-mouthing the OP to his girlfriend! These things rarely just go in one direction.

      • kerrycontrary May 20, 2013, 4:59 pm

        yup, I can imagine “Oh she has a crush on me, I tell her to stop flirting, she imagines that I like her, she’s crazy, etc…”

      • Lindsay May 20, 2013, 5:52 pm

        Yep. Would the LW want him to do that to her if they were dating? (Though this is where she’d say, “It’s only because they aren’t happy. He wouldn’t do it to me.”)

  • Liquid Luck May 20, 2013, 3:37 pm

    You know, Tim could be absolutely perfect, and you could have an awesome relationship. Maybe it’s everything you’ve both been looking for for a long time. But the reality is that HE doesn’t think it’s worth the risk to his friendship to find out, and you can’t make him choose you. Honestly, it sounds like he’s keeping you on the hook. He’s happy with his girlfriend and his best friend now, but if a day comes where those relationships end, he wants to keep you around so he won’t be alone. You’re worth more than that, so find someone who actually wants to be with you NOW, and not in some hypothetical future

    I firmly believe that there isn’t just one person out there for everyone. There are lots of people who could be a good match for you. Sure, Tim could be one of them, but he’s not the only one and he’s proven that he doesn’t want to be with you (by actively choosing not to be with you). So stop spending time with him alone, tell him that you don’t want to hear about his feelings toward you since he’s obviously not prepared to do more than bring them up just often enough to keep you wondering “what if,”, and let this go.

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  • Miss Terri May 20, 2013, 3:39 pm

    Whoa – I almost lost track of what was going on! But I agree with Wendy – cool off and let things take their course. It sounds like ALL of you need to slow down and get to know people first before you jump into “relationships” with them… For all you know – you could hook up with Tim and realize that you don’t like him as much as you think – and then you have destroyed a long-term friendship. Definitely expand your circle of friends – hopefully you can find someone that doesn’t have so much drama….

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  • Sheryl May 20, 2013, 4:04 pm

    I would separate from both of them… if you really do think Tim might be a long term possibility, don’t hang out with Seamus anymore at all. The more time between you & Seamus’s fling, the more likely he’ll be able to accept you dating Tim (if it came to that).

    Also, I agree its kinda crappy that Tim is sorta of keeping you on back burner while dating someone else. By removing yourself from the picture, he can focus on his new girl to see if she is really right for him, but also see if you are just there for convenience, or it makes him realize he likes having you around, and wants to keep you around.

    Either way, by sticking around, you are creating an un-winable situation. If Tim tries to contact you after you disappear, tell him the truth. That you didn’t want to be responsible for breaking up a best friendship, AND, ya know, he is dating someone else! That would give him the opening to do something about it, and maybe after a few more months have passed, you could try dating TIm if he steps up.

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  • Lindsay May 20, 2013, 4:05 pm

    You say that Tim, for sure, has feelings for you, but this honestly sounds like when I was in high school and my friends and I would convince ourselves that our crushes had secret feelings for us but were being held back by some unseen obstacles. In reality, they just weren’t that into us. Maybe Tim does like you, but if he’s with his girlfriend and not you, then I think you have to assume that he either doesn’t like you THAT much or likes his girlfriend more than he lets on. I think that it’s best to take what people say or do at face value.

    The idea of secret feelings and stuff is an interesting plot line for TV dramas and rom-coms, but not really in real life. In film, it’s sexy and dramatic, but for real people, it usually means someone is a wuss, or wishy-washy or, for whatever reason, the two people are just not a feasible couple.

    So, WWS.

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    • Lily in NYC May 20, 2013, 4:55 pm

      LOL, we used to tell each other that “he’s just intimidated by you because you’re so self-assured and intelligent”! Yeah, right. I look back now and laugh at my 18-year old self.

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      • ktfran May 20, 2013, 5:26 pm

        Wait? What? You’re telling me the reason he isn’t with is not because i’m super intimidating? Just, what?

      • Lindsay May 20, 2013, 5:49 pm

        Hahaha. That’s exactly what we said, too.

  • painted_lady May 20, 2013, 4:37 pm

    Eh…I mean, this is obviously null and void if Tim isn’t feeling it, but I’m contrarian enough that I’d want to see if Tim reciprocated my feelings simply because it bothers Seamus. Even if you were really dating him, it would still be borderline controlling to say you couldn’t date Tim (I get that it happens, but it’s not really fair). But you weren’t dating. Again, that’s me being a contrarian asshole, so maybe don’t listen to me. In my eyes, friends dating ex-FWBs isn’t a friendship-breaker. Hurt feelings for a few months, yes, but then you get over it. And if you can’t? It’s not the responsibility of the other parties involved to be your wet nurse.

    HOWEVER…it could be argued that you also weren’t feeling it enough to make a move on Tim when he was single and you and Seamus were kaput. It would be one thing if you and Tim were humping like bunnies and he didn’t make a move, but it sounds like there’s never even been confirmation that you reciprocate his feelings. Wendy is right that Tim has more to lose, and if he’s been putting out feelers and getting nothing back in return, he’s not likely to make a huge unambiguous gesture that risks both his friendship with you and his best friend. So as the party who has less to lose, well, what have you got to lose? I say go for it. If he’s not into it, he’ll say and you’ll either be fine or you won’t, but really, if he’s going to be an immature jerk and make it awkward, who wants him? And Seamus will either get over it or he won’t, but again, who wants to be friends with that guy who would end a friendship over you guys going after what makes you happy?

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  • Holly May 20, 2013, 4:59 pm

    The only thing keeping me from thinking this was about my ex-boyfriend was the line “they’ve been living together for six years.” *shudders*

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  • Addie Pray May 20, 2013, 5:03 pm

    LW, I think you should confess your feelings to Tim (if you haven’t already). I know, some people will disagree with that because he has a girlfriend but meh, just do it. Then update us.

    Also, is Seamus a real name? I have never heard of it. I have a weird name so maybe I’m not allowed to point out other weird names.

    Also, Wendy, can we have a Singles-themed week? You could focus on lonely girls, lonely girls with cats, lonely girls with empty bottles of wine, and bitter gay men. Ha.

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    • kerrycontrary May 20, 2013, 5:13 pm

      AP, did you not read/watch Harry Potter? Seamus Finnigan! Get with it.

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      • Addie Pray May 20, 2013, 5:32 pm

        Whoops! Obviously I do not read or what Harry Potter. One day I’ll get with Googling shit before I show my stupidity by asking what it means first. (One day in the future, not soon).

    • ktfran May 20, 2013, 5:24 pm

      Bitter gay man. Singular AP, singular.

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      • Addie Pray May 20, 2013, 7:21 pm

        Well I hope for our favorite bigger gay man there is another bitter gay man out there for him!

      • Addie Pray May 21, 2013, 9:16 am

        *bitter, duh

    • Wendy May 20, 2013, 5:09 pm

      We do have Singles-themed week on DW. It’s called every week!

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      • Addie Pray May 20, 2013, 5:32 pm

        Oh good point.

    • lets_be_honest May 20, 2013, 8:05 pm

      Its a very Irish name, pronounced Shay-mus.

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      • Addie Pray May 21, 2013, 9:17 am

        oh i love it!

  • lets_be_honest May 20, 2013, 8:07 pm

    I don’t get why you’d want to date someone who has no problem talking about his current girlfriend to the girl he’s flirting with. Weird.

    I think landygirl said it best. There are other fish in the sea. Find one whose not all up in this mess.

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  • Boosker May 20, 2013, 9:55 pm

    The fact that he had a girlfriend but took you on a grilled cheese date makes me distrust this Tim character. This is not an attack on grilled cheese, which is delicious.

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  • Trixy minx May 21, 2013, 1:03 am

    Just walk away from this whole mess. If he wanted to be with you he would. This reminds me of the letter writer that dated twin brothers in high school and was still infatuated with one.

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  • kare May 21, 2013, 2:26 am

    All I could think about throughout this letter is “I’ve never had a grilled cheese”. Perhaps I should get on that?

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    • Fabelle May 21, 2013, 8:38 am

      WHAT. You need to go make/buy one right now!!

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  • SasLinna May 21, 2013, 6:14 am

    Stop spending time with Tim for a bit. You might get over your feeligns if you stay away from him for a month or two and focus on what else you can do to make yourself happy. Crushes feel much stronger when you’re living your life in a circle of friends/acquaintances and don’t venture out of that circle. You’ll automatically stop thinking about Tim if you don’t allow yourself to feed your crush on him anymore. Who you fall in love with is much more circumstantial than you think – if you get into a different environment you’ll likely find someone else there.

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  • Jess May 21, 2013, 9:38 am

    OK, I missed all this yesterday but have a slightly different perspective so figured I’d open my yap.

    Sometimes in small social circles, when you are in your 20s (guessing) and really feeling ready/eager for a stable committed relationship, you start to see romantic prospects everywhere. First you discovered a mutual attraction between you and Seamus. Then you “wanted more” and he didn’t. It’s natural in this situation that your brain sort of looks for a way give this misfortune some purpose. Maybe your FWB experience with Seamus was MEANT to lead you to Tim. But see, when you find yourself moving from one to another in a small circle, and when you find yourself seeing prospects in people that were previously friends (or tangential to an earlier connection), it’s often that you are just rummaging through the same haystack looking for a needle that probably isn’t there.

    It’s happened to me enough times, lord knows. Like others said, it may just be time to find new haystacks and keep your eyes open for a shiny needle. Stop wasting time on hay stalks.

    (Did my metaphor hold up?! lol!)

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  • Miss T May 22, 2013, 9:57 am

    I don’t like this. If you have any respect for either of them, you will leave this whole situation alone, remain casual friends with them and be find other guys to date. I hate to rain on the parade of destiny, but if Tim was the guy for you, he would have gotten together with you when things fizzled out with Seamus. When two people truly want to be with each other, they get together and overcome the obstacles. When one or both just enjoy a flirtation and don’t want anything more, they do what they can to keep the status quo. This letter was a very long, dramatic version of “I banged one guy while flirting with his best friend, and now I want to bang the best friend but he has a girlfriend. Can you reassure me that this is okay?” It’s not.

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  • BreezyAM May 28, 2013, 1:30 pm

    Seamus is frankly irrelevant to this conversation. I am so sick of people acting like toddlers over dead relationships no matter the sort. Especially a “fwb” thing, especially over a year later.

    You LW need to find a new dick, because you have no idea what will go down with Tim and don’t want to start any potential relationship under THAT cloud.

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