“We Break Up Every Month. Should I End It For Good?”

My boyfriend, “Robert” (32) and I (31, f) started dating in February of last year. From the get-go, I had this feeling of doubt. During our first year together, almost every month, I told him I simply couldn’t get rid of the doubt and then I broke up with him almost each month; we then got back together a day or two after each break up.

In May of last year, a lady friend from Robert’s hometown texted me saying that there were rumors that he and his ex (39) were still in contact, probably getting it on, but she had not seen them together and she had no proof. I confronted him and he told me that he would not entertain gossip. I broke it off as I believe that where there’s smoke, there’s fire.

In December of last year, we broke up for ten days. I was mad because Robert didn’t make plans with me for the holidays. I was working and he went to visit family in another town (his excuse being that he asked me what my plans for the festive season were and, when I told him I’d be working, he didn’t see it necessary to make plans with me). However, we continued having contact during this period and I eventually told him I’d clear my head during my annual leave.

On the 29th, I went on leave for two weeks. During this time, I had no contact at all with Robert as I had no reception where I was. He did send me text messages which I later read when I got home. One said, “I don’t feel like living anymore.”

In January of this year, he begged me for us to work on our relationship as he said he saw a future for us. I agreed as I do love him, but the doubt was still there. During the year, we’ve grown closer (only one breakup for three weeks, which was in April, and we made up as we usually do). But by the end of September, the doubt was back and I told him I’m out for good and that this is the final breakup. He suggested we try couples therapy and I declined.

A few days later, a “voice” told me to google-search his ex. To my shock, one of the first results was a brand new photo of her and Robert at their baby shower. I was devastated!!!!! I confronted him by phone, he denied it, and, when I told him I could send him the photo, he confessed. Technically, I was not supposed to care as we had split up for five days, but I had a meltdown due to the shock.

I asked him how far along she was and he told me that the baby is due in a week. He said that they hooked up and had a-one-night stand during one of our breakups (this was not a justifiable reason for me as he know we always break up to make up). He said he wanted to tell me in August when she texted him about the pregnancy, but a few days later I was in a car accident, after which he helped me to recover and we were happy together and so he didn’t wanted to hurt me.

He asked me to forgive him and I did, but I told him that I will not be able to trust him again as I did not cheat during any of our breakups. Surprisingly, I feel sorry for him. I told him that he needs to prepare himself for the life-changing experience of parenthood and forget about me, and he said he will wait and see if the baby is really his.

I offered my shoulder to cry on as he sounds down in the dumps. I do love him a lot. But I do not think we will get past this situation. I specifically told him when we met that I don’t date guys with children because I don’t have time for baby mama drama. Please, please, please: your guidance would be much appreciated. — Having Doubts

I’m not sure what you want me to say? By your account, you never trusted Robert – even from the “get-go” you had “doubts.” You’ve broken up – what? — ten, twelve times now? You “break up to make up” and consider it cheating if either of you has relations with anyone else during one of your breakups. So… are these not really breakups? You actually believe Robert when he tells you he had only a “one-nght-stand” with his ex during one of your breakups? I mean, come on. You’re 31 and behaving this way? It’s time to grow up, stop being naive, stop being such a drama addict, and stop being so freaking passive.

Nothing at all – not one thing you wrote in all these paragraphs (and all the ones I edited out for brevity) suggest you’re an active participant in your life. For example, you get mad at your boyfriend for not making holiday plans with you after you tell him you’ll be working and then you breakup with him for two weeks when he does his own thing. It’s like you’re setting him up to fail. When someone asks what you’re doing and your hope is that you do something with him, fucking say that! Don’t say, “I’ll be working,” which indicates that you don’t have time or interest to make plans. When you break up with someone, BREAK UP. Don’t hold your partner to the rules of a monogamous relationship if you’re actually broken up. And if you aren’t actually broken up, don’t call it a break-up! Call it an argument or taking some personal time or whatever.

I mean, really, this is all basic being an adult 101. If you don’t even have these very rudimentary skills of functioning in an adult relationship, I’d take Robert’s suggestion for therapy and run with it (except, go solo – not with him). You cannot take these awful skills of manipulation and dysfunction from your relationship with Robert and apply them to the next relationship. You have to learn how to be a grown-up who trusts her gut, follows her instinct, clearly expresses her needs, and respects boundaries. You have to grow up. And if, at 31, you haven’t been able to do so on your own – either because you lacked good role models growing up or you’re really immature or you’ve been deeply damaged in some way and need help healing – it’s time to get the professional support that will get you where you need to be in order to have successful, happy, functional relationships.

I’m coming across incorrectly in my communication with women. I went to a speed dating event last week and had no matches — not even with the woman whom I had some things in common with and when the conversation went well. My thought process was to ask about hobbies, interests, and what they enjoy doing for fun. In my mind, if we have some common interests, then we are at least dateable — to spend time together, to learn more about each other. Since some of the women had to take a moment to think about what their own interests are, I started asking what they’re looking for in a man and in a relationship. Again, some had to briefly think about their own answer. I was at a singles party (Lock and Key, if you’ve heard of it) last month, and, again, I found no one wanted to date.

My results are similar online. Even on Match.com, where activity is made visible to me, I have changed my profile three times, and every time I write multiple women who read the message and view my profile but do not respond.

What is the proper approach to talk to women? — Not Matching

My gut feeling is that you are probably treating women like potential job candidates that you’re interviewing. Your line of questioning is likely coming across as very goal-oriented, which is understandable since your goal is to find a match or someone to date. But when you think about getting a match or getting a date as the ultimate goal, you suck any potential fun out of the equation and you ignore the better goal of seeing if there’s a spark.

Finding a spark is one of those things that’s hard to quantify and even harder to manifest. In fact, it’s nearly impossible to manifest. The spark is either there or it isn’t. No amount of “correct answers” or even right questions is going to create the spark. The spark is created by chemistry – by something that is almost entirely out of your control. Your job, essentially, is to get out of the spark’s way – quick blocking it with your pursuit of a goal and let it do its thing. The key is, you really don’t need to say much at these speed dating events or even online. What you need to do is to present a great image – in person you want to dress well, groom yourself well, have a flattering haircut, have good breath, smell nice. Post photos on your dating profiles that feature you in good lighting, with a warm smile, dressed in flattering clothes, and occasionally in locations that give some indication what your interests might be.

Listen more than you talk. Respond to interesting points made in profiles or in-person conversations. Ask questions with easy answers, like: do you have any upcoming travel plans? Have you seen any good movies lately? Do you have any pets? These are simple conversation-starters that get you – and the other person – out of the way of a potential spark. The answers to the questions are almost irrelevant – except for their potential to lead to a conversation; the real point of them is to establish a neutral tone from which you can gauge attraction and chemistry. These things are actually more important than whether you share common interests. Interests can be established and can and do change over time; chemistry is either there or it isn’t.

Finally, the “proper approach to talk to women” is pretty much the same as talking to anyone. Women are people, after all. We aren’t a great mystery you need to solve. And if you’re meeting women in specific spaces created for match-making, whether it’s online or in person, there’s a good chance the women are feeling a lot of the same things you are: a little (or a lot of) anxiety, some excitement, maybe frustration. Focusing on putting others at ease can have a wonderful effect of putting yourself at ease, too (and, again, makes space for that spark to shine). When all else fails, “you have a great smile,” is a simple way to ease a little tension.

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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. The first letter was edited for brevity? You’ve broken up countless times. You have had a feeling from the start something’s wrong. He’s about to be a father with his ex (ex?). It doesn’t seem like you even like this guy! You are broken up – you need to remain broken up. And, the whole broken up/cheating thing just reminds me of the whole Rachel/Ross debacle on Friends. If you’re broken up, it is not cheating.

    1. All I could think of was Ross and Rachel as I was reading this. Crazy town!

  2. Ele4phant says:

    LW1 – I think you’re the side piece here, tbh. I don’t think his ex is or ever was “an ex”.

    Look you’re too old for this. Don’t waste time dating someone you don’t trust. You’ve wasted a year of your life on a man you’ve never trusted.

    Come on, grow up here. Remove yourself from this situation. Make better dating choices in the future.

    1. Yeah, this guy is by no means a saint, but the LW sounds exhausting. Their relationship sounds like a vicious cycle of neverending high school drama. Stop being a drama queen, LW, and consider therapy.

      1. ele4phant says:

        Yeah, he’s no prize, but LW is writing in, and LW there’s plenty you can do to not be in this situation.

        End the relationship, and take a good hard look at the choices you make so you don’t make similar choices again in the future.

        Like Wendy said, you have agency to direct your own life. Use it.

    2. golfer.gal says:

      I agree. From the anecdotal research available on this site, one night stands should be recommended as a treatment for infertility given the astronomical rate of pregnancy that results. LW 1, you are definitely the other woman. He’s continuing to minimize with this ridiculous “one night stand” lie, and apparently it worked because he’s still in your life.

      I agree wholeheartedly that you need to make some changes and get some help before you attempt another relationship. Listen to Wendy and seek counseling. A good partner is going to run fast and far from your behavior and you’re going to be stuck with another sleazebag.

      1. ele4phant says:

        To say nothing of the fact that the ex is 39. It’s possible, I’m sure, but becoming pregnant becomes harder and harder once you get past 35, right? Many couples at this age have to actually put in effort to get pregnant. Not necessarily medical interventions (although many couples need that too to become successfully pregnant in their late 30s), but fertility tracking, timing, waiting and trying for a long time.

        It’s possible this woman randomly got pregnant after a one night stand, but not probable. The chances that he has had an ongoing relationship are very high. Furthermore, it might even be PLANNED.

      2. Eh, I think that’s kind of dated info about how hard it is to get pregnant after 35. I think after 40 that’s true, but I know lots of women who got pregnant easily between 35-40 (myself included: I got pregnant twice at age 38 – one pregnancy ended in miscarriage; both times, as soon as I tried) and of the people I know who had trouble, their fertility struggles preceded turning 35.

        That said, I would be shocked if this particular pregnancy was the result of a ONS!

      3. “one night stands should be recommended as a treatment for infertility” is just ….so….perfect.

      4. ele4phant says:

        Fair enough. I;m not over 35 yet, nor have I yet done anything less than actively try to prevent a pregnancy , so I don’t really know what I’m talking about. Although glad to know it can be not as hard as I’ve heard since I’m close to that age and I may at one point want to, well, not try to stop pregnancy.

        But we can all agree, this likely wasn’t a one-off.

        And seeing as the ex was around first (and is the one he’s having baby showers and publicly acknowledged the pregnancy to his friends and family with), chances are SHE’S the “real” girlfriend and LW is…not.

      5. I also doubt it was a one-night stand, but LW fails to understand that when she breaks up with a guy, all commitments to fidelity disappear during the breakup. She childishly ‘breaks up’ but doesn’t mean real break-up. Huh? As she writes, she is the initiator of all of these break ups. And she expects them to be viewed as punishment where he just sits home alone until she decides he’s been punished enough. It’s rich that she says because of the ex’s pregnancy from the ‘one-night stand’ she can never trust him — she made it clear from paragraph one that she never trusted him from day one. She just stayed, with all her doubts and her infantile break-up punishments. They deserve each other, but seriously a permanent MOA should have happened at the first break up.

      6. Avatar photo Skyblossom says:

        I agree with Ron. She was being dramatic and punishing him for whatever infraction she felt he had done. The whole thing was so very juvenile. Lack of her presence in his life was supposed to make him into a better partner or at least make him grovel enough that she would take him back. She must have come from a terribly dysfunctional family.

      7. Ruby Tuesday says:

        Six months into my parents’ relationship, I surprised my mother when she became pregnant at 38. My dad once joked “And she said she couldn’t get pregnant.” I replied “And you believed her.”

        My sister followed two years later with zero issue. My parents will celebrate 35 years of marriage on Groundhog Day.

  3. Avatar photo Skyblossom says:

    LW1 Where did you learn such a dysfunctional manner of communication? When you didn’t like something you broke up instead of talking about whatever issue you had and coming to a resolution. That is so dysfunctional. It is dysfunctional to the point you will never have a good relationship unless you quit doing it. You have to learn to talk, like an adult.

    Unless the two of you specifically agreed that when you broke up you weren’t broken up you were broken up and he was free to do whatever he wanted with whoever he wanted. If you want someone to be monogamous you don’t breakup with them every time you get annoyed. You had no understanding that there would be no sex when broken up. You’ve applied that standard after the fact. Don’t break up unless you intend to be done with the relationship. No adult would take you seriously as a romantic partner.

    Also, aim higher. If you don’t trust him don’t stay in a relationship with him. The guy who would hide an entire pregnancy isn’t worth your time. But, you will probably be mad for a few weeks and then get back together. He knows it and you know it. That’s how you handle relationships.

  4. I suspect, but have no proof, that LW #1 is stuck in some pseudo-rom-com mentality. I can’t imagine at 31 still believing that people have ESP. If you need something, you have to say “I need this.” From the outset LW #1 was making her boyfriend fight for her… no one should have to put that much effort into a relationship in the first 3 months. I’m exhausted just thinking about it.

    LW #1 if you want someone to chase you, steal their wallet, otherwise you’re just playing games.

  5. I was so exhausted after reading the first letter that I almost didn’t read the second one.

  6. If you had doubts from day one and break up every month, then this isn’t going to work. MOA. A guy you’re dating texting you that he doesn’t want to live is another sign to bail.

  7. Avatar photo Moneypenny says:

    LW1: This is the plot to a soap opera, right? Right?!?

    1. Sea witch says:

      Has to be. Maybe she watches them all the time and mistakes that sort of drama for normal life? Why stay with someone you have so many doubts about? Was he the only (seemingly) single man in town?

  8. anonymousse says:

    Even before the pregnancy mic drop my advice would be YES. Break up….for good! Block him. Make an appointment with a therapist to discuss why you would be in a relationship in which you don’t trust your partner. It turns out your tuition was onto something- he is having a baby with someone else. He’s likely in a long term relationship with that woman. Why else would they be taking photos together at the shower?

  9. Sea witch says:

    “He said that they hooked up and had a-one-night stand during one of our breakups (this was not a justifiable reason for me as he know we always break up to make up). ”

    Break up to make up??? Who does that? Why on earth would he think that your breakups were only supposed to be temporary?

    1. Right? What does that even mean? This is one of the most dysfunctional relationships I’ve ever heard of.

  10. Sea witch says:

    Not matching: If you wish to find a future lady who will birth strong warriors to defend your lands and estates, you must set three tasks for the potential candidates. One task must require thought and clever problem solving, another physical strength, the third fighting prowess. Above all your future lady must be capable of giving birth, so ask for a fertility test as well.

    As the candidates leave the room in a hurry to get away from you, you can judge their running speed and use it for points in the physical prowess category.

  11. LW1: So. Much. Drama. Is this really how you want to live your life? You mention “only one breakup for three weeks” like it’s a good thing. And by the way, if you’re broken up, there’s no cheating, because you’re broken up. I have news for you: this is not normal. Break up for good and then go to therapy to figure out why you think it is. And don’t date for a while. Really.

  12. LW1: Periodically avoiding the guy but keeping an expectation of sexual and emotional fidelity isn’t “breaking up to make up”. It’s giving him the silent treatment, which can be really psychologically damaging. If you care for this guy, you should probably either 1) stick with him until/unless the time comes for a permanent breakup, 2) realign your expectations to casually affectionate companionship with no promises of commitment, or 3) break up entirely.

    I’m also scratching my head at how you don’t want to date guys with kids, this guy has a kid from an encounter that you consider cheating, and yet you still want to stay with him. I hope you don’t think that you can make him stop being a father. That’d be cruel to him and to the child.

  13. LW1, Drama much? Just let the guy go and block his number/email and move on with your life. All of that was ridiculous…you never trusted him, you broke up over and over, he was cheating on you, and now he’s about to the a father. This is not how a healthy relationship works. Dump the guy forever and move on. Next time find someone more mature who is not a cheater!

  14. You have issues. Reading your post, I thought that you were a terrible girlfriend. Break up like this all the time, on a whim, on a doubt: what an abuse to him. Then I read that he is expecting a child with an other woman, but begs you to rekindle with him. He is as crazy as you. It is like a sado-masochist repetition of the same pattern: you are both nuts. Just start a therapy ASAP, to work on yourself and on the concept of healthy relationship. Let him sort out his own life.

  15. LW2: your questions are boring and too ordinary. Just start a conversation and see how it flows and where it leads you. Or ask a few questions that are out of the ordinary, a bit as a funny challenge that your date would be a bit thrilled to answer. Don’t ask so early what the other person expects in a relationship: way too soon.
    For your profile: ask a few female friends their opinion. Let them (and some guy friends) make your portrait (in words) and pick up some ideas. Work on your pictures too.
    There are coaches online who will help you to introduce yourself more efficiently.
    At the end of the day, if you come across too much like: I am looking for a date, any date, then it is not attractive. Women want to feel chosen, that you have options and that you like them especially, that they rise your interest. Ask yourself wether you like them, not wether they validate you.

  16. LW2 actually has a long thread in the forum- https://dearwendy.com/topic/how-do-i-properly-communicate-with-women – where he reveals a lot more details about what he wants and if you read all of his comments, and there are a lot, its pretty clear what his problem is.

    It’s not simply that he’s talking to women in speed-dating and online dating apps like he’s interviewing for the position of his girlfriend. Its that he is interviewing for that role with very specific and rigid expectations in mind about what he wants to do with that girlfriend, as well as considerable urgency about finding someone quickly – which probably comes across as desperation.

    Basically, he is very into going to holiday activities, specifically Christmas parades and light shows. Like, wants to go every day into it. And he wants to find a girlfriend who will do that with him – before the holidays this year. And he appears to be basically interviewing every women he meets with questions about their interests and hobbies in the hopes of finding someone who will enthusiastically want to go to these parades and light shows (and, at other times of years, other different holiday activities). He has made it clear he does not simply want someone who would be willing to go to some of these activities with him, he wants someone enthusiastic about it – otherwise he would feel like he was dragging them along against their will.

    I am sure his obsessive-sounding focus on the parades and light shows comes across as quite creepy, so I am not surprised he is having little success.

    The bottom line is correcting his online profile of changing his approach to talking women is unlikely to be enough. He really needs to rethink what he wants from a relationship, because currently he only seems to rigidly want a holiday activity buddy who will do all the stuff with him he does anyway, and that is not how relationships work. Even if he gets a woman to go out with him, they are unlikely to stay unless he rethinks his very rigid current expectations about dating (as numerous people in the forum have pointed out.)

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