Dear Wendy
Dear Wendy

Morning Quickies: “Should I Tell My Friend/ Co-worker/ Former Hookup That I Hooked Up with His Roommate?”

About three months ago I realized I had feelings for my co-worker, Joe. He left our job but then came back years later. One night Joe asked me to come over to his house to hang out. We ended up Netflixing and chilling. It was great, but I worried about any awkwardness at work. So I decided to tell him that I have feelings for him and to ask him if he likes me. He said yes but that with everything he’s been through with his ex he’s trying to focus on himself. Then he led me on for the next month or so. We hooked up again. Then, out of the blue, he tells me his ex is pregnant. I still have feelings for him at this point so I ask him point blank, “Do you want to be with me? Yes or no?” He says no as if he never liked me at all.

A few weeks go by and his roommate hits me up on snapchat. At first, I didn’t know I was talking to Joe’s roommate But then I saw him on his roommate’s snapchat story. I told his roommate that Joe and I had hooked up, and to my surprise his roommate doesn’t care at all. So we actually hooked up recently. I have this honesty pact with Joe. We tell each other everything. We’re very open with each other, which is why I wonder if I should tell him I hooked up with his roommate. but Joe is a moody guy sometimes, so I don’t how he’ll take it. His reaction could be that he doesn’t care or he might mad at me and end our friendship. Should I be honest like always and tell him or should I take this one to my grave? He’s also been avoiding me for two weeks now. He walks past me at work and doesn’t say anything or look my way. — Take it to The Grave?

Yeah, so you and Joe aren’t friends. He used you for sex, led you on (although I don’t know how you can call it that when he preceded the leading you on by telling you he only wanted to focus on himself) and for two weeks he’s been walking past you at work without even acknowledging you. That isn’t how friends behave – at least not friends you have to be so concerned about sharing your secrets with. And, anyway, Joe probably already knows that you hooked up with his roommate – it would explain why he’s been suddenly ignoring you at work. But if you’re looking for a sign that he’s bothered by this news – that he’s jealous, maybe – in hopes that it may indicate some feelings for you, don’t hold your breath. If the guy had feelings for you, he would have taken you up on your implicit invitation to pursue something more than a casual hook-up. He didn’t, and he doesn’t (have feelings, that is). You need to MOA – from Joe AND his roommate.

I’ve been dating a guy for a year and a half now. We have known each other for 17 years and were first intimate years ago, before we ever made it official. The problem is that we were having an argument the other night and I brought up his ex. They were together for six years and he and I literally started talking and hanging out the week they broke up. So I asked him the burning question I’ve always wondered: “Would you be with her still?” His answer, after about 25 long seconds: “I don’t think I could ever try again. But I still love her. It just wouldn’t work.” Ouch.

So basically he would choose her over me. That’s how I took it anyway. I caught him texting her about six months ago and we broke up for a couple months over that. Even though he says it was nothing. My question is: Should I just end the relationship because I’m second choice? That’s how I feel anyway. And I hate it. Or do I stick it out and become the woman he ends up loving more, maybe?

Thank you so much for any input. — Second Choice

Ok, new Dear Wendy rule: If you write in about the same significant other more than once (or, in your case, twice), the automatic answer is MOA, period.

Also, no, he’s not telling you you’re second choice. He’s telling you he’ll always have love for his ex whom he was with for six years. The fact that you feel, after a year, that you don’t measure up and that you aren’t his first choice is reason enough to MOA. The fact that in the year and a half you’ve been together you’ve already broken up for a couple months and are contemplating it again is reason enough to MOA. And the fact that this is the THIRD time in one year’s time that you’ve written for advice about the same guy is, in accordance with DW law, reason to MOA. Period.


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

23 comments… add one
  • JD January 31, 2019, 9:07 am

    A man hasn’t led you on if he flat out said he doesn’t want more. Just because you try to manipulate the situation by assuming sleeping with him can “change” his mind does not mean you were led on. He, rightly, assumed that when he told you this, you accepted it and still wanted some booty. He assumed that based on your actions. I honestly feel bad for men (as it tends to happen to them more) when they are clear and women just think they can change their minds, then make them out to be the bad guy for “leading them on” while they were upfront the whole time.

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    • Cara January 31, 2019, 8:49 pm

      He did lead her on. A yes but…is not an actual answer. If he liked her but didn’t want a relationship he should said “I like you but I don’t want to be with you”. Some guys aren’t upfront. They give half answers. He could point blank told her he just wanted to hook up and wasn’t looking for a relationship. I mean what was the point of telling her he liked her?

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      • JD February 1, 2019, 7:03 am

        No, saying “I don’t want to be in a relationship or anything serious” is very direct. For your sake please hear and understand that.

      • anonymousse February 1, 2019, 8:35 am

        He didn’t lead her on.
        Their first hang out was to Netflix and chill.
        She asked him if he liked her. He said yes-but he needed to focus on himself. “Yes, but” is in fact a real answer.
        They continued to hookup. She made the choice to keep hooking up with him. And then slept with his roommate.

      • ele4phant February 1, 2019, 12:26 pm

        “He could point blank told her he just wanted to hook up and wasn’t looking for a relationship.”

        But…he did tell her that he didn’t want a relationship when she asked. I’m sure he does like her and enjoyed her company, otherwise he wouldn’t want to have sex with her at all. You can like someone and not want a relationship with them, and that’s precisely what he told her.

        It seems like you think he should’ve stopped hooking up with her because she wanted more, that he should’ve taken on responsibility to protect her from her own feelings. But she’s an adult, not just capable but responsible for looking out for her own welfare.

        If being in a causal relationship when she wanted more was going to cause her pain, it was her job, not his, to set boundaries and call it quits.

        He gave her all the information she needed, she decided to stay in this hook-up arrangement knowing full well that’s all he wanted. If she wasn’t cool with that, she needed to stop.

  • JD January 31, 2019, 9:10 am

    LW2: I feel the same way about my ex. I will always love him and wish we could have worked out. That doesn’t mean he was right for me, it means I cared for him and loved him as a person so it’s a shame. My husband is well aware of this and feels zero insecurity over it. I assure you he wishes it could have worked out with his ex wife, but it couldn’t. I would rather have a husband who wished his marriage would have worked then was damn happy it ended.

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    • Rava January 31, 2019, 11:41 am

      YEEEESSSS to this.

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  • Carolina Blue January 31, 2019, 9:11 am

    Both LWs are beating dead horses. I know it’s hard but aim higher and MOA.

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    • JD January 31, 2019, 9:16 am

      Aim higher than nice men who are upfront, honest and have feelings? Sounds like both will be reaching for the stars.

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        Bittergaymark January 31, 2019, 10:40 am

        Yeah, the men here with these two simply aren’t the problem…

      • Carolina Blue January 31, 2019, 11:51 am

        I should say they both should want better than trying to make a relationship with people who don’t want a relationship with them. You can’t force a connection.

  • brise January 31, 2019, 10:46 am

    I don’t think the first man (Joe) is nice. He is a taker. I don’t like his double dating and his suddenly claiming that his “ex” is pregnant. Come on – not honest.
    But the second guy is nice and genuine. LW2 is obsessional. Why focus so much on an ex? Why such an insecurity?

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    • anonymousse January 31, 2019, 11:10 am

      He was pretty obvious with what he wanted and was willing to give. There first hang out was to Netflix and chill. He said he was focusing on himself.

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    • anonymousse January 31, 2019, 11:10 am

      He was pretty obvious with what he wanted and was willing to give. There first hang out was to Netflix and chill. He said he was focusing on himself.

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    • Ele4phant January 31, 2019, 10:28 pm

      Eh, he was upfront about what it was he was willing to give. She took him up on it knowing she wanted more, that’s on her.

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  • anonymousse January 31, 2019, 11:04 am

    Why sleep with Joe’s roommate who searched you out because you slept with Joe? Like…why? I say this because you don’t mention anything in common or anything that struck your fancy about him. Did you sleep with him solely to make Joe jealous?

    Don’t get involved with men at work. Even if you catch feelings.

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  • anonymousse January 31, 2019, 11:07 am

    LW2 if you seriously have written in to Wendy multiple times about the same person, you should know this is too much work.
    He actually comes off as very forthright about his feelings. Did you really want him to lie to you instead? Nothing he said indicates he ranks you as second, although with the insecurities you have….maybe you shouldn’t date anyone with a significant ex.
    Please MOA.

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  • ron January 31, 2019, 11:35 am

    LW#1 – Nothing really wrong with dating a co-worker, if you don’t take your fights to work, which he now has. Nothing necessarily wrong with dating your ex’s roommate, although in this case you’re clearly not over your ex and I agree that you hooked up with his roomie just to make him jealous and now want advice on how to tell him to get the desired result. He already knows.

    While serially hooking up with or dating guys who are friends or roomies not inherently wrong, it does indicate that you are fishing in an extremely small pond.

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  • dinoceros January 31, 2019, 12:06 pm

    LW1: He didn’t lead you on. He told you he wasn’t interested in a relationship and you continued seeing him anyway. YOU lead you on. Also, “honesty pact”? He’s not your boyfriend. There’s no reason you need to have a pact where you tell him everything. It’s none of his business. Stop obsessing over him.

    LW2: Don’t ask questions you don’t want to know the answer to. Also, I didn’t get the same message from his answer that you did. It sort of sounds like you were going to interpret his words the same way regardless of what he said. If you feel like you’re the second choice and aren’t OK with it, then yes, dump him. But honestly, if you’re in a relationship where you are already convinced before you talk to the guy that he prefers his ex over you, then it’s really silly to still be dating him.

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    • kat15 January 31, 2019, 12:59 pm

      “Don’t ask questions you don’t want to know the answer to”

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      Lucidity January 31, 2019, 2:04 pm

      Agree that the message LW2’s boyfriend was trying to convey was not the same as how she interpreted it. It probably wasn’t terribly smart of him to be honest with her, given her issues with jealousy and insecurity, but this is how people often feel about their exes, especially when the relationship lasted a long time and ended on fairly good terms. My husband and I will always love/care about the people we dated seriously before each other, although we’re no longer in love with them. We remember the relationships fondly and while we regret that they didn’t work out, we also wouldn’t go back and try again because we wouldn’t be together now had those relationships been successful. We touch base occasionally with our exes, but are not threatened by that contact.

      Most people on this planet come with a past. There is enough room in their hearts for you AND the memory of their past loves. If you can’t handle that, date someone who has never had a girlfriend before.

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  • kat15 January 31, 2019, 12:58 pm

    LW1 – For future reference, “trying to focus on himself”=not interested. And you don’t need to worry about whether to tell him about hooking up with his roommate, he not only already knows, he probably steered the roommate toward you. Sorry to be harsh, but this guy was upfront and you aren’t listening. It’s no reflection on you (unless you keep pursuing him), he just isn’t into you.

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    • Ele4phant January 31, 2019, 10:36 pm

      “He probably steered the roommate towards you”.

      I was thinking this too! Like, why else would the roommate randomly reach out to you unless he thought you might be the type that’s up for casual hookups.

      Not to say that Joe was like – hey LW1 is easy and I’m done there so if you want my sloppy seconds go for it; but I’m sure the roommate was aware you and joe had a casual thing, he probably knew joe was done, and he probably ran it by joe to get the okay before reaching out.

      And Joe may not be talking to you because he knows you have stronger feelings than he does and he’s trying to not encourage you anymore. You didn’t respond to his kinder gentler rejections so now he’s full on freeze out, because that seems like that’s what it’s going to take.

      I’m sure he’s not upset you hooked up with his roommate.

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