“My Boyfriend’s Sending Selfies To Another Woman!”

I have been with my boyfriend for over two years. I know the entire time we have dated he’s been cruising Craigslist and gives his first name and phone number to women seeking a causal encounter (red flag). I choose to ignore this behavior because it seems like the women never follow through with his requests. I monitor his phone and his Internet, email, and Facebook accounts daily. Recently, he accidentally included me on a selfie text he sent to another number. I found out it was a woman who works at the same company he works at but on a different shift. I further found out that she is married with children. I contacted her. I told her if she continued to mess with my boyfriend, she would ruin her family. I further told my boyfriend to leave me alone.

The woman swears she doesn’t know who my boyfriend is and, if I wanted to, I could call her or her husband and talk to them. Funny thing is, just five minutes after I messaged her my boyfriend was calling me telling me I was crazy and that I misunderstood (red flag). He said she was just a friend he texts with. I hung up on him. But now I’m starting to think I may have over-reacted. I feel bad for making accusations to the woman that may not be true. What are your feelings on my situation? Should I apologize to the woman? I already have trust issues because of the Craigslist ordeal. — Seeing Red Flags

You know, for someone with self-described “trust issues,” you sure do ignore some serious and obvious “red flags,” as you call them. And what you call a “red flag,” like the first flakes of an imminent snowstorm, I call an avalanche of signs that this guy is not trustworthy. And if you’re someone who guards your trust to the point that you monitor your boyfriend’s every fucking digital move, I can’t believe you’d choose to ignore that your boyfriend seeks out women wanting “casual encounters” on Craigslist. This is quintessential burying your head in the sand!

What’s even the point of monitoring his every digital move when you already have the dirt on him? He’s cruising Craigslist on the regular and sending selfies to at least one co-worker and who knows how many others. And then he’s lying to you about it. Because he knows that if you have a bigger issue than your trust issues, it’s your fear of being alone. What other explanation is there for staying with a guy like this? What other explanation for calling out the woman he was texting instead of HIM? Why else would you tell her that her family would be ruined if she continued texting your boyfriend, but say nothing to him except “leave me alone” — and then worry later that you “over-reacted”?!

Girl, you need to MOA, stat. And then get yourself into therapy and work out why you’d stay with this loser as long as you have.

I broke up with my ex (whom I dated for three years) for good in August after having two short breakups earlier in the summer. We continued to live amicably with each other until November when he moved out. Between November and April, he and I would still hang out as friends and occasionally hook up with each other.

A week after our last hookup in April, he wasn’t being as communicative through phone and text as he normally was, and I got suspicious. I confronted him and he told me he had a girlfriend who he had been dating since February and they had become “official” in March (just a week after he and I had spent three nights together).

I want to be able to continue the friendship we had when we first stopped dating because we still have so much in common, but now I can only see him as a cheater, on both me and his current girlfriend. I’m still not sure if he ever told her he hooked up with me when they were already in a relationship and, if he did, that I had no idea he was seeing her. Should I message her about it and let her know she is dating a cheater?

It makes me so miserable knowing he is so happy with her and that he really screwed me over. — The Cheater’s Ex

He didn’t screw you over. You dumped him and you two became friends with benefits. Those benefits don’t include commitment or monogamy… because you dumped him! He didn’t really owe you anything, except maybe letting you know whether he was sleeping with other people and potentially exposing you to STDs — not because your relationship warranted that, but because common decency does. But you also could have asked if he was sleeping with anyone else, and I’m assuming you didn’t, or you wouldn’t be all shocked now that he has a girlfriend.

Surprise! Someone you dumped nine months ago moved on! Why on earth you think this means he cheated on you, I don’t know. After you break up with someone, if they sleep with someone else, it’s not cheating. You do realize that, right? As for whether he cheated on his now-girlfriend: that’s not your concern. Maybe she knows about it already. Maybe she doesn’t. Maybe, since the overlap between his screwing you and starting something with this woman was relatively brief — a few weeks, really — it falls into enough of a murky area for him to justify his behavior. Or maybe it’s something he can’t justify and he feels guilty about it. But that’s all his business and not yours. It’s not your business. HE and his love life are not your business anymore.

I’m sorry you feel miserable seeing your ex-boyfriend so happy with someone else. But you broke up with him, so what did you expect? That he would remain your friend and sex buddy indefinitely (or, more likely, until YOU met someone else you wanted to get serious with)? If you wanted him to remain loyal to you, you should have remained his girlfriend. But, I assume you had good reasons for not staying in that relationship. Remind yourself of those reasons. Remind yourself why you no longer wanted to be his girlfriend and why it’s actually ok that another woman who presumably DOES want that role is filling it.

Bottom line: He moved on. You should, too.


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


  1. Juliecatharine says:

    WWS. Additionally, ladies can we knock it off when it comes to dragging other women into your nonsense? Deal with the person you’re in a relationship with.

    1. Stilgar666 says:

      Right?! These are not complicated situations

  2. Avatar photo meadowphoenix says:

    1) Your boyfriend wants you to break up with him. He’s not accidentally putting you in a group text. This is the cowardly way to do it, but honestly this is your decision. If you’re not okay with this, fucking leave.

    2) Nah, I would be pissed too if someone I was sleeping with didn’t tell me they had a girlfriend. You can see in the question RIGHT ABOVE that that’s getting you involved in a third-party’s potential craziness. No thank you. And I think the burden of tell a FWB that they are committing to someone else falls on the person committing. I would def think less of a person for this.

    But yeah, otherwise, he didn’t cheat on you. You can’t assume commitment especially when you deliberately stopped the committed aspect of this. Leave this other chick alone.

  3. artsygirl says:

    LW1 – so your BF has a long history of at least attempting to cheat on you, and your response when seeing HIM send a pic to another woman is not to confront him, but is to track down the other woman. Seriously? You have to fucking babysit your BF like a toddler because he cannot respect you and your relationship but you threaten to torpedo another woman’s family? You have no idea if she requested the image, or if she is in an open marriage, or anything else – basically your BF is shady as fuck and instead of taking ownership of your complicity since you refuse to dump him, you lash out at another woman. Get your mind straight.

    1. LW1 – I think you fall victim to some really bad thinking when it comes to men and women. Society tells us that there are these slutty women out to steal our men and that the women are to blame and the men can’t help themselves. You need to look at how you frame your relationship and yourself in the world. Please understand that there are good men in this world that when faced with temptation, won’t cheat. You deserve better than this but I would start with looking at what you believe you are worth and what women are worth in this world.

      1. Both your comments — BINGO! Why not hold the actual cheater accountable for his actions? It seems like there’s a good number of women out there who’d rather last out at the other woman instead of confronting their man. The problem isn’t the “slutty women out there to steal our men” as csp is observing; the problem is dating or being married to someone who doesn’t respect you and or the relationship!

    2. artsygirl says:

      Just as a quick note – no do not call this woman and apologize. You have already strayed into bunny boiler territory and continuing to reach out is likely to make her feel even more uncomfortable. Just hope that she will one day be able to laugh off the psycho girlfriend who called her up accusing her of cheating and threatening her family life.

  4. LW2. Ugh y’all are not friends. Can we stop with this “I’m so evolved I can be friends with my ex” and call a duck and a duck. Your still sleeping with each other, your still involved. You wanna know how to be friends? Quit sleeping him. Give yourself some time to oh I don’t know, actually get over the relationship before trying to be friends. You played yourself and now your paying the price for not being honest

  5. Avatar photo Raccoon eyes says:

    LW1: Dear Lord, your bar of acceptable behavior is low. Please please please dump this guy – lose his number, block him everywhere possible, and get yourself to therapy like Wendy said. Aim higher – leaps and bounds higher, please – you are worth it. This guy is NOT.
    LW2: Look, the moment I read that he was suddenly distant, I knew where this was going. Actually, I was pretty sure where it was headed from the first line… Anyway, please dont try to play the Holier Than Thou /Self-Righteous Card about this- be honest: you wanted him around as long as YOU wanted him to be, not on his own terms. You lost this one, Buttercup. Dont be THAT girl. Leave him and his new ladyfriend alone- yes, it feels like slinking off to lick your wounds, BECAUSE IT IS. You WILL get over this- dont wallow in it.

  6. Northern Star says:

    LW 2: You say you want to continue the “friendship” you had when you first stopped dating your ex. Does that include having sex with him? Because that was never a reasonable expectation. He didn’t “screw you over.” You weren’t committed—specifically, you were UNcommitted, because that’s exactly what you wanted.

    He probably is a liar and a cheater, but you are motivated by your own feelings of betrayal to bust up his relationship. And I don’t think you are justified to be so hurt.

  7. LW1: What is the fucking POINT of monitoring his online behavior if you’re just going to stay with him no matter what? You are wasting your time policing all his Craigslist activity if your plan is to just put up with it. You could at least take up yoga or knitting or learning Italian instead of reading through the daily evidence that your boyfriend is cheating on you, information with which you intend to do nothing. What would it take for you to actually dump him? Good lord. Aim SO MUCH HIGHER.

  8. ele4phant says:

    LW2 – I mean I’ve been in your shoes. I know how you feel, but just because you feel it doesn’t mean you’re in the right.

    After my college boyfriend broke up, we continued to hook-up. Until one day he told me he had a new girlfriend. I was PISSED, because how dare he?!

    With time, I realized he was well within his rights to move on. We were not a couple anymore, we had no commitment to one another anymore, and we both had the right to move on if and when we found someone else we were interested in. He found someone else first. He also wasn’t being sneaky or lying to me. He told me, as soon as he was sure himself, that our arrangement needed to end because he wanted to get serious with someone else.

    And if I was being honest with myself, I was still emotionally attached and it was a bad idea on my part to fall into a casual arrangement with him. But that was on me, not him.

    It hurt, but he wasn’t being hurtful. Just like your ex isn’t.


    1. ele4phant says:

      Also – not that it’s your business anymore, but how are you sure he “cheated” on her with you? When you start dating someone new, you don’t necessarily immediately jump into being exclusive. Sounds like he has not had sex with you after he became exclusive with her. You guys weren’t really in a relationship, so he didn’t really “owe” you a breakup or explanation. He just stopped sleeping with you.

      Doesn’t sound like he necessarily did anything wrong to either of you.

    2. LW2 – I have been in this place too. It feels like you deserve more transparency because you have such a history. I had a guy that I had a FWB thing for years. We went to high school together and whenever we were in town on breaks and after we graduated, we fell back into seeing each other. Then one day, he was like “I’m moving to DC next weekend” and I was hurt because he didn’t even bring up to me that he was thinking about moving and we had known each other for years! We talked and saw each other a few times a week! But I realized that I had grown more attached then I realized. So he left and we stopped talking. Nothing dramatic happened but it really hurt in private. Funny story, He called me like 2 years later and I got to tell him I was engaged….sooooo petty of me but I just loved telling him.

  9. I know I sound like a broken record on this, but LW1 is like a case study in people who cling to a spectacularly bad relationship without a moment’s thought as to whether it’s worth having. It’s “I can’t lose him, what if I lose him”….but why the hell do you WANT him?

    If someone told you up front, “If you get involved with this guy, you will spend your days monitoring his phone calls and texts and social media accounts, and he will spend his days looking for your replacement.” Would you even go on the first date with the guy? Of course not.

    So why are you clinging to him now? There’s no honor in staying with someone who has no respect for you, who doesn’t even care enough to be faithful. You don’t get bonus points for loyalty for being a doormat.

  10. I love the whole “I’m not worried about his attempts at cheating, because nobody likes him enough to respond” Yeah because watching him trying to cheat on you with other women is much better than him actually cheating. That would make me feel so shitty to know that my SO knows I can see everything, and still does it. But you created this situation, so you have to be the one to leave it.

    Not sure what’s worse, that or telling yourself and the world that you completely broke up with somebody when you are still talking to them all of the time, and fucking them. And then accusing them of cheating on you when you broke up “for good”.

  11. also LW2: if you still lived with him amicably, were great friends, and slept together, why did you break up?

  12. LisforLeslie says:

    This all sounds so exhausting.

  13. dinoceros says:

    LW1: I’m very perplexed. What’s the point of tracking your boyfriend’s online behavior if you don’t care that he tries to cheat on you? I mean, you know for a fact that he contacts women online about sex (even though you THINK he hasn’t acted on it). What’s the point of checking his social media? What purpose does it serve? Generally, the purpose for most people would be to inform them of whether their partner was being sketchy, so they could break up with them. Have some standards.

    LW2: He didn’t cheat on you, and he may not have cheated on his girlfriend (you don’t know their arrangement). If you break up with someone, you don’t get to control whether they see other people. You made a poor decision by continuing to hook up with him and act like a couple because now that he’s moved on, you still haven’t. You should try having a real breakup with him.

  14. Avatar photo Dear Wendy says:

    From the LW:

    Thanks Wendy for your response. And yes I am afraid of being lonely. I am a widow. My husband died of cancer almost 5 years ago when I was 43 and he was 45. We have 3 boys age 24, 20, and 12. For almost three years after his death no one would ask me out or even call and talk. I was a (and still am) a very lonely woman. You see in the past 5 years I have lost 3 jobs, put my oldest son through rehab twice, almost lost my house, lost my car and tried to maintain the (somewhat) relationship with the “red flag” guy. When I met him he gave me some much needed attention that I couldn’t ignore. And so my feelings are truly that I do hate the thought of being alone. But I am a better person. And I do deserve happiness maybe more than some. I have been in therapy and diagnosed with codependency. I have read so many books on the subject but I continue to fall prey to the never ending “blaming myself” for others actions and reactions. So I know what to do. I just hate rejection. But I have stuck to my guns and have not talked to my ex. Wish me luck.

    Thanks again
    Seeing Red Flags

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