“I’m in Love With Two Men: One’s Married and the Other is a Drunk”

I am in love with two men. They both say they are in love with me, and I believe them. They don’t know about each other. One is married, and we got together before he admitted that he is still married. He says he wants to be with me, not her, but I’m not naive. If he weren’t married, he’d be perfect. But there’s the fact that he *is* married, at least for now.

The other man is not married, but he’s an alcoholic. He’s financially stable and very intelligent, and we can talk about everything. But his sex drive is almost zero.

Both men have suggested open relationships (man #1 because he lives so far away and we never see each other and man #2 because of his lack of sex drive). So I don’t feel like I am cheating on either of them exactly. If I could somehow combine them into one man who was single, not an alcoholic, but had all their other traits, it would be so simple. But the fact is that I am very much in love with them both.

I never in a million years thought I would ever find myself in such a situation. I’ve always been a good person, always played by the rules. I never even dated while my son was growing up because I didn’t want him to become attached to some boyfriend only for us to break up. I was single for fifteen years; now I have two boyfriends, and I don’t know what to do. — Between Two Guys and a Hard Place

I can’t imagine you are fulfilled by either one of these boyfriends. First, you hardly even see one and he’s married to someone else. The other has no sex drive and is drunk all the time. You were single for fifteen years, during which time you played by some rules you thought you had to follow in order to be a good mom to your kid, and now that he’s grown you’re ready to break rules and have some fun. The ironic thing is it doesn’t sound like breaking the rules — that you didn’t have to follow in the first place! — is bringing you any fun. And there’s a strong possibility your actions are contributing to the pain of another woman. There are better ways to sow your wild oats, my friend, than carrying on with some long-distance lover you never see and having a side relationship with someone who doesn’t want sex.

I say break up with them both, get yourself to therapy, and take up more thrilling hobbies to fulfill your need for an adrenaline rush after fifteen years of playing by the rules: take up skiing, go skydiving, do some solo travel, get a tattoo. And remember the old Dear Wendy quote from years ago: “If you have to choose between two people, the answer is probably neither.”

I’m 27 years old, and over the last six months I started a new job and met a co-worker who’s 25, mature, and looked promising. From the first day we talked, we clicked. We had a lot of things in common—likes and dislikes, being able to finish each other’s sentences/knowing what’s in each other’s mind, etc. Even though we’re in the same office, we have texted 24/7. We even had sex a couple times, which none of our office-mates know of. They even thought we were a couple, but we’re more like close friends with benefits.

Our texts were all hot and sexy and usually initiated by him. On the weekends, he even wished me a good morning. We had some real conversations as well. It was nice and poetic at first. But then in the third or fourth month, things started to change. It seems like he has lost his interest in me. Nowadays, he doesn’t even text me…

He gave me mixed signals from the beginning until I got attached to him. He said himself that he wasn’t ready for marriage or a serious relationship; I get it, but sometimes I want a guy to care about me like a boyfriend. I had a bad and ugly past relationship, and was I hoping that this was the one…someday.

My friends told me they saw him with another girl in my office while I was gone and saw other girls texting him. I started becoming needy and jealous. He kept giving me all guy excuses like he’s not seeing anyone, they are all just friends, etc.

I don’t want to jeopardize our friendship for my own unnecessary delusional feelings. I enjoyed being with him because I get him and he gets me. All my friends and family told me to get over him or move on; I tried but I can’t because he’s always there right in front of me. I can’t just quit my job.

I don’t know what to do anymore. I’m sick and tired of having the same kind of relationship, tired of crying to myself and making a fool of myself. I’m on the verge of making him distant and ruining the friendship that we had, which I don’t want to do.

Help me. Tell me what should I do about it. — Waiting for The One

Friends shouldn’t make you feel horrible about yourself. Friends shouldn’t make you cry or make you feel like a fool. You shouldn’t feel needy and jealous with a friend. This guy isn’t a friend. He’s someone you hoped would be your boyfriend, but you settled on sexts and “good morning” texts on the weekends and a few random hookups, hoping eventually he would want something more. He didn’t, he doesn’t, he won’t. There is no friendship to ruin. There is only your self-worth and dignity to ruin, and carrying on like you have been is doing serious damage to both.

Yes, distance yourself from this guy. Delete his number, stay away from him at work, ask your friends not to talk to you about him. Move on. He doesn’t love you. Not even as a friend. If all he did was sext you, sex you, and wish you good morning on the weekends, he’s not your friend. I’m telling you as clearly as I can: you do not need a friend like this. Friends worth having are ones who support you through your trials, celebrate your victories, hang out with you regularly with your clothes on doing stuff that doesn’t involve sex or hooking up. Friends have so many “real conversations” with you that it’s unnecessary to point out that you have “some real conversations” in addition to hot and sexy text conversations. This guy is not your friend. Find your dignity and self-respect and cut him out of your life for good.

I have a friend I went to school with. We were never close, but we’re cool with each other, and years later I’m a barber in the barbershop he goes to (not his barber though), and we have some mutual friends. We never hang out outside the barber shop — once in a while he will send me a funny FB message, but that’s the extent of our interactions with each other. Ten years ago he dated a woman for almost two years, and she and I became really cool with each other. They broke up, she got married, and, she told me, her husband told her she had to get rid of all her guy friends. My friend ended up getting married, too, and had two kids. Eight years later his ex got a divorce (no kids) and we ended up re-connecting on FB. We’ve hung out a few times, just catching up. My friend found out we texted and is not happy about it. He doesn’t know we hung a couple times. I honestly don’t know if we would end up dating, but we always were really cool with each other. Should I still hang with her? I wouldn’t if I were actually closer with with the guy (maybe he thinks we are?). I enjoy hanging out with this girl — we have great conversations and fun times. What do you think? — Old Friend Flame

I think it’s ridiculous that grown adults are telling people who they can and cannot hang out with, especially so many years (and marriages and kids and divorces) after a relationship ended. You like this woman and enjoy her company, and the feeling seems to be mutual. You don’t seem to care about the old school friend who goes to your barber shop. Would it upset you if he no longer considered you a friend? If he stopped coming to the barber shop? If he stopped sending you an occasional message on FB? If he talked shit about you to mutual friends? That’s really your biggest risk here if you continue hanging with his ex-girlfriend from ten years ago. If you can handle those risks, I say go for it — keep hanging with the woman whose company you enjoy. Maybe you’ll end up dating and maybe you won’t. Maybe you’ll catch up a couple more times and that will be it. Maybe she’s enjoying her new-found freedom post-divorce and, once that novelty of that wears off, so will whatever spark that has reignited between you. If you can handle the thought of that at the risk of alienating a casual friend who frequents your place of business, there’s nothing else to lose. And if he’s the kind of guy who would give you shit for texting a woman he dated ten years ago like he owns her, maybe he’s not someone you would miss having in your life anyway.


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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.


  1. Bittergaymark says:

    LW1). Eh, just enjoy them for what they are, I guess. Eventually — you’ll tire of of one (or BOTH!) of them and move on. Or they will tire of you. At any rate, somebody will get tired… Not every relationship needs to go anywhere. NEWSFLASH: Most of them don’t.
    LW2). I pointedly disagree with Wendy here. This guy is NOT making you cry. YOU are making yourself cry. So just stop it. You were fucks with benefits. It was fun while it lasted — but start being a little aloof for Pete’s sake.
    LW3). Tell your friend to grow the fuck up. Seriously. Heterosexuals seem to thrive on needless ex drama. Honestly, I don’t get it. The fact that vapid breeders waste so much time an energy on this shit is why we have Trump in office. People are stupid. Worse, it’s seemingly all they aspire to be as of late.

  2. LisforLeslie says:

    LW #1 – You don’t have two choices here, unless you live in a 2 horse, no traffic light town in Wyoming, there are likely hundreds if not thousands of men who are better suited than a married man or a man who can’t satisfy you in bed. Aim higher.

    LW#2 – The lesson here is Don’t shit where you eat. There’s a reason the saying exists. Hold your head up high. Don’t feed the drama. Don’t gossip about him. You had a connection. He’s moved on. You have to move on too.

    LW#3 : BGM this drama is not solely within breeder-land. That said: Exes can’t claim perpetual dibs on someone they dated. You like her, she likes you. Who cares what your not-much-of-an-acquaintance-that-you-see-when-someone-else-cuts-his-hair thinks? Anyone who gets the story will know he’s a fool. Leave the fool alone and do what makes you happy.

  3. Anonymous says:

    LW2: Focus on your work and ignore the guy, treat him professionally as a colleague. And date out of your office. This will simplify your life. You are hurting about this guy, it sucks, but he isn’t worth your tears. He isn’t interested, and you can let him go in concentrating on your work. Each time you start thinking of him, just think that, and invest in your social life out of office.

  4. dinoceros says:

    LW1: But do you really have two boyfriends? You spend time with two men who are each committed to someone/something else? I don’t think this is as much a crazy turn of events, as it is you for whatever reason seeking out available men. Have some standards and break up with them both.

    LW2: I don’t think he gave mixed signals. He was never interested in anything more than friends with benefits. Then he either decided he wanted to spend more of his time with someone else, potentially because he realized you wanted more and wanted to cut that off. I can’t tell if you actually want to be friends or you just would miss him, but you can’t have a healthy friendship with someone who you are into who just wanted sex. You’ll always be feeling something negative. It’s not worth it. There are other people in the world to be friends with.

    LW3: What Wendy said. It doesn’t sound like you’re close with this guy, so who cares if he doesn’t like it?

  5. LW 1- Dating a married man is wrong and very bad karma. It will come for you, so you should RUN before it does. As far as the alcoholic goes, alcoholism is progressive and very, very difficult on loved ones. No one can get an alcoholic to go sober, but the alcoholic. I have been through this, I have lost several loved ones to alcoholism. (when I say lost I mean like DEAD) I would not wish the experience on anyone , so I would say to run away from that one just as quickly.
    You are old enough to have a grown son, you should be old enough to know better in both instances. There is someone better for you out there.
    LW-2 There are office “playas”, this guy probably is one and he has moved on…so should you. Like the other comment said “don’t shit where you eat”. It is hard not too because you are there 8 hours (or more) a day, but it is almost always a VERY bad idea.
    LW-3 WWS

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