“When Do You Know It’s Time to Break Up With Someone?”

When do you know it’s time to break up with someone? I hope by virtue of asking it’s not the time, but I also don’t want to hear what I think might be your answer. I’m 28 and have never been in a relationship until now, no flings or anything. I was busy with school and work and did some online dating, but nothing stuck. I’m also a virgin. I met my boyfriend about five months ago online. Initially, I wasn’t sure if I was physically attracted to him, but he was really nice (also funny, smart, etc.). Still, he wasn’t my type as far as I knew, but I wasn’t ever disgusted by him, so we kept going out. My physical and emotional attraction to him has grown, but I’m having doubts.

I don’t know if I want to marry him, which is ultimately my end goal, but can you really know after five months? If I were 22, maybe it’d be different. I’m not urgently rushing to get married but, sure, in the next four to five years, yes. He’s the first for everything sexually for me except kissing. It’s been fun. But I’m concerned that the hormones and oxytocin are clouding my judgment and since he’s my first and it’s new and exciting, that’s why I’m still feeling this “chemistry.” We have fun on our dates. He’s also really affectionate, which, I hate to admit, is nice.

There are some things we need to figure out, like culture and religion, though we have lightly talked about this. But there’s no point talking about it if I think we should break up. I know you don’t need a reason to break up with somebody, but if I had to pick one, the only reason would be because I can’t picture marriage yet. I’ve given myself a six-month deadline, though I dread that coming up. I also don’t want to waste his time or mine. But I’m just not ready yet to break up. I’m afraid I’m getting attached. What is chemistry? Are all his good qualities enough to outweigh some lesser physical attraction?

Thanks for your advice. — Not Sure about Marriage Yet

There’s something going on here that you need to get to the bottom of before you can have a happy, healthy, successful relationship. The facts that at 28 you’ve never, ever been in any kind of relationship until now, that you pursued dating this guy because he “didn’t disgust you,” that you’ve given yourself a six-month deadline — on your first relationship! — to decide whether you want to marry your boyfriend, that you “hate to admit” that the affection you’re getting is nice, and that you don’t seem to be very physically attracted to your boyfriend and think that any chemistry you’re feeling may be attributed to the newness of finally being physically intimate with someone all suggest some unhealthy attitudes toward intimacy, relationships, marriage, and, ultimately sex. You mention religion and culture only as some things you need to “figure out” with your boyfriend, so I don’t know how much religion and culture have played into your love life — or lack thereof — but is it possible you’ve been taught to feel some shame around affection and intimacy? Have you been raised to believe that marriage is the ultimate goal and that “good on paper” is the best predictor for a good match? I wonder if you’ve ruled out better matches for yourself because they didn’t fit into whatever box you thought a potential spouse should fit into. Do you even know what or whom you’re attracted to? Are you sure you’re even straight? These are questions that might best be addressed in therapy or, if you’re particularly religious, with a clergy person or other members of your faith.

You don’t need a reason to break up with someone, but if you did, you have a few reasons that are more compelling than not being able to picture marriage yet with someone you’ve known for five months. Top of the list, in my opinion, has nothing to do with the guy but entirely with you, and that’s that you might not be ready for a serious relationship yet. You have nagging doubts, you can’t decipher what true chemistry feels like, you’re concerned that the newness of the relationship is clouding your judgment — all of these things are related to your lack of experience and not really knowing what it is you truly want, and maybe to not giving yourself permission to experiment.

It’s like if you’ve been thirsty all your life and someone finally gives you a glass of milk to drink and your thirst is quenched to a degree, but you aren’t sure you even like milk or if you just like not feeling so thirsty all the time. You know there are lots of other beverages to try: water, juice, tea, coffee, lemonade, even alcohol. But for some reason, you’re like, “Nope, I’ve got this milk here and it’s not terrible, so I’m going to give it one more month and see if I want to spend my life drinking milk forever and never try anything else.” That makes no sense. Drink some damn lemonade. Try some coffee. Live on the edge and have a beer. There’s a whole world of liquid goodness and you might find one that satisfies you like you can’t even imagine because you’ve never let yourself think about that kind of pleasure.

Look, there will always be milk — if not the glass you’re currently consuming, then another. I know it may not seem like it because you were 28 before you let yourself taste it, but that was your own doing. You were afraid of the milk. You were afraid of all the drinks. Milk was the safest and so you tried it and good for you. But I think if you let yourself take some more risks and try some different beverages, the pay-off is going to be pretty great. Might you try something that isn’t so great? Sure. There might be a lemonade that’s too sour or a whisky that burns going down. You will survive. And you’ll learn about what you don’t like, which is as important as learning what you do like. Right now, all you know is that milk is fine. It’s nothing special, but it’s something and that’s better than nothing. I say keep looking for special. There are lots of varieties of drinks and there’s one for you that will not only quench your thirst, but also will erase all doubts that you’ve found your favorite.


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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. dinoceros says:

    I think a lot of people who don’t have much experience dating don’t feel like they have a right to be picky (for lack of a better word). It feels like it’s a lack of self-esteem, in which a person thinks that they must not be much of a catch, so they have to take what they can get; the perception that the future will be the same as the past, and a person to date won’t come around again for years; or they just don’t have any point of reference to understand what a relationship is supposed to feel like. I don’t know if any of these apply to you. It’s an odd contradiction for you to say that you feel like you may be clouded by this excitement, while at the same time saying you like him because he isn’t disgusting. While you list several nice traits, you don’t really seem like someone who is infatuated with this guy because most of the time, people who truly are clouded by this stuff are really into the person they are dating. You sound like you like the company and that he’s nice on paper, but little else.

    On one hand, having a six month deadline to know if you want to marry someone is excessive. At six months, you just need to know if you potentially could see a future with someone (if a future is what you want). You know, there are no dealbreakers, you very much enjoy being with them and enjoy who they are, and you feel compatible. You don’t need to know for sure that you want to marry them or not. It’s way too soon. That said, I’d say that you are coming up on the point where you need to have better reasons to date someone than just them not being disgusted and liking human warmth. It’s not a waste of time to date someone that you can’t commit forever to yet, but it sort of is to date someone who thinks you’re really into them and you’re not.

    1. TeacherNerd says:

      Indeed. Sometimes one DOES know at the six-month mark (I did, but I was also in my mid-30s and had 15 or so years of dating under my belt, so to speak), but I never started out thinking, “Well, I’ll definitely know within six months…” Some relationships will take longer for you to know that the other person is the right one; some might take you a lot less. If you’re not sure that the guy was someone you wanted to marry, then he wasn’t the guy (at least, not right then).

    2. For me I don’t think it’s the lack of esteem, but lack of reference point. I realized after I sent the email that the “didn’t disgust me” was not what I wanted to say at all (but I did, didn’t I). He’s very kind, interesting, motivated, and he’s also open about his feelings. I also feel comfortable with him which maybe an attraction thing, but I’ve told him things I’ve never told someone else before. There are reasons why I’ve been dating him for five months! But I probably am not infatuated with him. I don’t think I’ve been infatuated since university, and that was when I was too shy to talk to guys so I built them up in my head.

      Re six months, totally know that is arbitrary but what you wrote about not having to know for sure just yet is really relieving, thanks.

      Wendy is probably right, that I’m not ready for a serious relationship. I wish I were after so long. I have my interests and I was content being single. But somebody had to be my first to find someone right? It’s not that I haven’t “let myself” tryother liquids. I haven’t really had a crush on anybody since school but I’ve gone on online dates. I’ve turned down second dates when I knew I wasn’t feeling it. Guys have turned me down. I went out on five dates with someone and also ended it because I wasn’t feeling it. I wanted to give this a try because this guy was so kind and sweet and also advanced things physically, and there could’ve been something more.

      But overall, no, I heard what I needed to hear. I probably should’ve done this three months ago. Now I have to find the words and the right time. And he is really into me and yes I will have bad dating karma.

      1. You will not have bad dating karma. It’s okay to feel things out for a bit — that’s the whole point of dating!

        Six months isn’t a terribly long time to date someone, but it’s also not insignificant. I mean, how would you feel if you were super into your boyfriend and then found out that he was so unsure about you, that he wasn’t sure he was even attracted to you after all that time, that he was hoping strangers could tell him if your other qualities were enough to offset your less-than-attractive-to-him-ness? Probably not great!

        Breaking up with people sucks. Even when you feel like it’s the right thing to do, it’ can still be hard, scary, and sad — but we’ve all been there. It’ll suck, but it’ll be okay!

    3. dinoceros says:

      I don’t think you’ll have bad dating karma. It’s not THAT bad. I think if you kept on for years, that would be different. I think most people use this time (the first 5, 6, whatever months) to decide if they are compatible. There are a lot of benchmarks to where you might continue reviewing and deciding if you want to be with someone. It’s an ongoing process in trying to determine if you want to continue seeing someone and then later, if you want to continue committing. I definitely didn’t mean to imply that you are leading him on now, but I think the more time that passes, it does become more of a time water.

      I also feel like I’ve been in similar situations as you in that I dated someone longer than I should have because they were a good person, fun, etc. It’s not a big deal unless you mislead them or purposely string them long.

  2. I’m going to disagree with Wendy here.

    I think, at the beginning of a relationship, you should be head-over-heels for the other person. If you don’t have that now, you never will. It sounds like you just like the idea of having a boyfriend, he was nice enough and available, so here you are.

    He’s not the only man on earth, and I suspect that if you commit to him, one day you’ll meet someone and get that crazy butterflies feeling and you’ll feel trapped.

    I’m also going to throw this out there – full disclosure, I don’t know much about it: Have you considered the possibility that you’re aromantic? My understanding is that aromantic people are interested in friendships and physical relationships, but not romantic ones. The way you talk about getting married sounds pretty clinical, so maybe you can relate to this?

    1. Did you even read Wendy’s advice? She pretty much said that he’s not the only man on earth and she should get out there and find out what she likes. What is there to disagree with?

    2. Avatar photo Dear Wendy says:

      Yeah, you’re not really disagreeing with me though. I don’t think you necessarily need to feel head-over-heels at 6 months in, but if you’re lukewarm about the milk, you need to try some other beverages.

      1. My disagreement is that I *definitely* think she should break up with him. I agree she has some soul searching to do about her thoughts on relationships and marriage, but regardless, she shouldn’t be with this guy.

        I think you need to feel some passion upfront or you’re going to end up with a roommate and a lingering uncertainty about what else is out there.

    3. I would disagree with needing to be “head-over-heels” at the beginning of the relationship. My most successful one was one that started slowly. I knew he was a great guy and that kept me around but it was the shared experiences and putting in the time to get to know him that really made the switch to being all gaga.

  3. Avatar photo Skyblossom says:

    I wonder if it is because she doesn’t find him physically attractive so thinks she shouldn’t enjoy the affection.

    I think she is hung up on the fact that she doesn’t think he is attractive enough for her and is concerned because in spite of that she is still getting attached.

  4. LW – You seem a lot like me in the way that I am a mental person first and emotional person second. Do you like pros and cons lists because I LOVE them. anyway…
    There are some people, and what Wendy alluded to, that feel like it is hard to know something without comparison. I feel like you can evaluate this on your own and there are a few things that I think should be helpful:

    1.) start thinking about the life you want to build with a partner (any partner) – make a list. Do you want to live urban or rural? Do you want kids? pets? how important is religion and family? how often do you want to see both sides of the family? travel ? how you look at money and savings? Do you like going out or staying in? – all of these things fall under “good on paper” but those things do matter a lot. If you want children and want to go to church every sunday then have family dinner with your parents, those are a big deal. Really paint the picture of what you want your life to look like.
    2.) You should talk about these things all the time. Talk about what you want and culture and family and how that fits in the future. Can you live with the idea of all that stuff? you shouldn’t shy away from those conversations, you should talk about them a bunch.
    3.) If you enjoy your physical relationship, don’t feel like you need to verify that just because you are inexperienced. You can if you want to but don’t feel obligated.
    4.) I would take the pressure off your 6 month deadline. Instead, I would have a state of the relationship conversation. Ask your partner how he feels about everything and if he has concerns.

    I feel like the more you talk, the more clear this will become. Don’t doubt yourself. You will come to the conclusion soon.

  5. I think she judged PDAs until this relationship. Then she realized how great it is when it is you.

  6. Yeah, that stuck out to me, too. Like, wait, what!? Why is affection a bad thing? It’s a GREAT thing!

    You don’t sound excited about this guy at all!

    I don’t think you need to be able to picture yourself married to someone six months in for it to be the right relationship. At six months, it’s more like, do you have fun together still? Do you feel naturally at ease together? Are there any serious incompatibilities? Are your feelings strong and growing? Can you see yourself with him longer-term?

    I think it’s pretty telling that you’re still unsure you’re attracted to him. Attraction is one of the easiest things to figure out in dating (for me, anyway) because it’s either there or it’s just not. It can definitely grow, and I’ve experienced this, but I think if it’s not there pretty early on, it’s not going to get any better. It sounds like it’s not really there for you. And that’s okay!

    Anyway, I think there’s a better match out there for you, someone who, if you wrote in about him after five months of dating, you’d sound super excited about.

    If someone cited not being disgusted by me as one of the reasons he continued dating me, I’d be pretty hurt by that. It’s great that you want to be mindful of not wasting anyone’s time, but some of the details included in this letter make me think you’ve (likely unintentionally) passed that point.

  7. dinoceros says:

    I sort of assumed she was implying that she liked getting affection in general, but not necessarily from him. Like that she might be hanging on to him just to have someone to be affectionate with?

    But I do think that some of her ways of thinking or talking about relationships make me wonder if she’s not super comfortable with it.

  8. LW, you speak of your love life a bit like a line in your CV, with a five year objective… You take things by the wrong end. In a healthy way, first you meet someone, have feelings, explore the alterity (which seems totally excluded from your perspective, you don’t meet the otherness in the other), then, after some time, step by step, you take it to the next level.
    Stop taking your romantic life as a job interview. It sounds so sad and cold…

  9. Mainly good advice from Wendy, but I’ll disagree strongly on one point. You seem to have grown up in an extremely conservative/sheltered/anti-sexual religious/cultural group, which has stunted your social development. Don’t go to your religious leader for discussion/advice on this issue, for God’s sake don’t go to your religious leader if you suspect you may be gay, unless you relish the thought of being shipped off for possibly violent conversion therapy. Seek a conventional, non-sectarian therapist, somebody who in addition to helping you work through your personal issues can help to interpret contemporary mass culture for you.

  10. Let’s aim for higher than “he doesn’t disgust me”. Way. Way. Higher.

    Agree that you have some issues with sex you need to work through before a relationship.

  11. I’m curious how other people define chemistry, though. Anyone have a good one? I really don’t. I think it varies from person to person and have had conversations with my therapist about what it means *to me* to find a great connection, but I’m intrigued by what other people would say.

    1. Avatar photo Cleopatra_30 says:

      Chemistry withna guy is more than just physical attraction. For me it also encompasses the mental connection. I definitely think my current BF and I have that, it is reallt freaky and refreshing too to know we think the same, which makes the relationship a whole lot easier.

      1. I mean, I definitely agree it’s mental/emotional on top of physical, but don’t know how to explain it. I recognize it when I feel it and assumed that was true for everyone. The best I can do is say that it’s a sense of feeling like you fit/click/belong with someone, but that’s so vague.

    2. Yeah, my favorite relationship book, “Is He Mr. Right? – Everything You Need to Know Before You Commit” breaks it down very well.

      After a first date, it’s just like, could I see making out with this guy? Going on a weekend trip with him? Introducing him as my boyfriend to friends? Not like, would I do it right now, but can I rule it out completely?

      Then later it’s about ease of getting close; trust; sexual attraction; fun; mutual respect.

    3. Avatar photo Skyblossom says:

      I have chemistry with my husband in a way I’ve never had with anyone else. The first time I met him I was introduced and said nice to meet you and went on my way and I didn’t even really notice him. I just know it was him because later I got to know the members of his research group and he was the only tall, slim, dark haired guy in the group so looking back I know I met him.

      That fall he volunteered to help me with something and we walked across campus talking and that is when I felt the chemistry. I would say we just clicked. He was fun and witty and it was great to walk across campus with him and I was attracted at that point. I think there must be pheromones involved because there are many guys that are fun and witty and I enjoy their company but I’m not attracted to them. They are friends and nothing more where with him I wanted the something more. That’s why I would call it chemistry. There is something physical I can’t explain that goes with the mental aspect.

      Even now, after 30+ years, I get turned on by rolling up against him in bed. I think that’s chemistry.

  12. Northern Star says:

    If you see the basic parts of a relationship as negative or chore-like, you shouldn’t be in one right now. It’s not fair to the poor guy, who doesn’t deserve your non-disgust. I mean, how would you feel if he thought about you that way?

  13. Avatar photo Cleopatra_30 says:

    If the LW Is who I think it is, you have been luke warm on the guy from the start. No need to push it to try and make it work. Sometimes you meet a person who seems to have everything you want, but the chemistry just isn’t there. It sucks big time, I have been there, but it is way more fulfilling and less mentally draining when you meet the guy who feels ‘just right.’ No bad karma, this is dating. There will be others 🙂

  14. Theresa Foley says:

    It is likely that the LW comes from a very conservative, Evangelical family that promotes courtship instead of marriage. Young people are discouraged from dating until they were ready for marriage, and dating became a courtship with marriage as the end goal. The LW’s dilemma is that while her boyfriend is nice enough, after a few months of dating she realizes that she does not want to marry him. She does not find him physically attractive, and there are major areas of incompatibility such as religion. She would like to break up with him but does not want to commit “emotional fornication”, which means becoming emotionally attached to a man that she does not marry. The ideology of this “purity” movement is summarized in the book I Kissed Dating Goodbye by Joshua Harris.

    I would like to tell the LW is that emotional purity aside, you are not committing a sin if you break up with your boyfriend. Even though you have become emotionally attached to him, you do not have to marry him. He sounds like a decent man, but incompatible with you. You both deserve to marry compatible partners.

  15. wobster109 says:

    Don’t ask whether you should break up. This makes continuing to date the default choice while you wait for something – a fight, a religious difference – to start the break up for you.

    Instead ask whether you should date him. If you were not in a relationship with him, would you ask him out, right now, today, knowing what you know about him?

    You don’t need a reason to break up, but you do need a reason to date. Or else you end up wasting years on a relationship that’s meh ok but doesn’t quite fit.

  16. Wow, that was the most interesting letter I ever read about a relationship. And I think your answer to this letter are great! I would love to see the horoscope of the woman, who wrote these words. There must be a lot going on in her house. I think a lot of it could be explained and solved with consulting her stars. I hope she finds help in which way ever will make her happy!

    Love, cathy

    1. Good God, you actually believe in horoscopes?

  17. LovingMommy says:

    In my experience, dating requires a healthy mix between what your heart says and what your head says. My default is to use logic and I feel like I could have written that post when I first started dating. My advice would be to stop overthinking this. I agree with Wendy that you could probably benefit from dating other people since this is your first real relationship.

    After my divorce, when I was looking for my fiance, I found a couple of guidelines. I’m going to skip my main rule I lived by because it would require experience and a good idea of what you want. Here are 2 things that I think you can use to keep your head in it and give your heart a little more freedom.

    You know the bible verse: love is patient, love is kind…substitute each time the verse says love with your boyfriends name.

    I assume that one day you want to have kids? Is your boyfriend the man that you want your son to become or your daughter to marry?

    If you boyfriend is both of the above then why not try dating him without some of the pressure you be been putting on the relationship? Just go with if he is both of the above, rest confidently that he is good company and date him until you don’t want to date anymore? Don’t worry about wasting people’s time or what is chemistry, is this just because it is New, etc. If he is a good man and meets the above 2 standards then relax a little. And if he does not then get out there and try new things 😉

  18. oof, reading this was so painful, especially her describing her tepid attraction to the man.
    I feel like Wendy could have been a little bit more sensitive to the fact that sometimes people do need to grow their attraction to other people via emotional connection, however, the querent seems definitely to not know what she is attracted to,..
    or even what attraction feels like.
    But, yes, her description of not knowing how she feels is painful to read.

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