Is It Better To Have Loved and Lost Than Never to Have Loved At All?

woman walking on the shore, alone

After taking years off from dating to focus (ok, hide behind) raising my kids, I got your Finding The One Online and started dating again. I wrote a kick-ass profile as you suggested and met more men and went on more dates than you can imagine. It was a really fun experience! One of the first men I started talking to quickly became a good friend. I had decided not to date him because we had different life experiences and he was not what I thought I was looking for.

He is mid-30’s, never been married, and never had children. I am early 40’s, divorced, and have 2 children. When he asked why I would not at least meet him, I told him it was because I had my children and didn’t want any more and he was “undecided” as to whether he wanted any. I figured why put myself in that situation. He thought I was putting the cart before the horse, so to speak, but left the decision up to me. Eventually we started dating and have been in a relationship for 7 months now. It has been everything I wanted. He is my best friend, my lover, and someone who the communication with is better than I ever thought possible. I realized I have unconsciously been holding him at arms length because of the kid issue. We had a talk recently about moving the relationship forward and becoming more ingrained in each other’s lives. He thinks we need to step out of the relationship bubble, and see where this might go. So, I asked him what he wanted out of life.

He said the only thing he is not certain of is having children. He goes back and forth on the issue and wonders what happens if in a few years he decides he wants them. He then asked me what I wanted eventually. I told him someone to share my life with. And if he wants kids eventually, that isn’t him.

We are at an impasse now. I know I am finished with that part of my life, and he isn’t ready to give up the option. So, I broke things off with him. It has been really hard on both of us to say the least. I have been going round and round in my head over this decision. Part of me feels like why open myself more to this when we have different goals. Another part of me is unsure if I have given it enough time. I am not certain he is “the one” yet because I have taken things very slowly to overcome my fears. So, a part of me feels like if I am unsure, how can he make a decision as life-changing as not to have kids at this point in our relationship? I am truly conflicted as to where to go from here. If someone offered you an amazing relationship for 3 years, but after that 3 years is up, it had to end, would you do it? I know there is no guarantee he will want children, but I also know there is no guarantee he won’t. What do you think?


I think, Cheryl, that you put yourself in this predicament, knowing full well that your relationship could be doomed from the start.

You can’t really tell where a relationship is going until you’re knee-deep in it.

I also think that there was no other way.

And the reason I’m running your letter is not because I have a pithy, insightful answer that you’ve never contemplated before, but because your situation brings up a more interesting and universal question:

“If someone offered you an amazing relationship for 3 years, but after that 3 years is up, it had to end, would you do it?”

Really, you’re just rephrasing the question: “Is it better to have loved and lost than never to have loved at all?” (for what it’s worth, Lord Tennyson says ‘Tis!)

I’m inclined to agree, with reservations.

First of all, as I stated in my epic Rori Raye blog post, you can’t really tell where a relationship is going until you’re knee-deep in it.

If I wanted to insist in the first month of dating my Catholic girlfriend that we raise our future children Jewish, that probably would not have flown. But six months in, that same proposition didn’t sound as intolerable.

People, as you pointed out, Cheryl, make big concessions all the time for the right person. But that doesn’t mean that they’re always going to make those concessions.

Long-distance couples start intense relationships, but break up because each presumed the other would move.

Interracial couples start intense relationships, hoping for their family blessings that never actually come.

And, of course, people fall deeply in love with highly flawed partners — the drug addicted, the chronically depressed, the perpetually unemployed — hoping that they’ll change once they’re married. They almost never do.

Which brings us back to your dilemma and how you should handle it, Cheryl.

If you were in your 30’s and you were the one who wanted to have children, I’d tell you to exit a relationship with a man who was “unsure”. That’s a wild card you simply don’t want to play, no matter how much you love him. My wife’s first husband decided he didn’t want kids after they were married, which is about the shittiest thing you can do. (Besides cheating, which he also did.)

The only way to get a big reward is to take a big risk.

However, you’re in your 40’s and are a mother who doesn’t want to be a mother again. You’ve been there, you’ve done that, and you’ve got the vomit-stained T-shirt.

This gives you all the power in the world to date for love’s sake — to have a beautiful relationship without being needy or clingy or fearing the future. You can simply enjoy the present in the same way you’re enjoying it now.

Doing so will present the greatest odds that you actually get to have your cake and eat it, too. Because your boyfriend may find himself so enamored with you that he couldn’t imagine life without you — and that’s why he will consider sacrificing the idea of having kids. However, if you start pressing him for answers right now because you’re afraid of wasting time, the whole thing’s going to backfire on you.

This is a dichotomy with which many women struggle, and yet, it’s the only way. You don’t make demands on a guy to figure things out on your time table. You trust that he cares about you, you make your relationship as safe, fun, and nurturing as can be, and you have the greatest possible chance of getting what you want.

The alternative is dumping him now to find another man who doesn’t want more kids, but I have a feeling that you’re not too psyched about doing that.

Are you taking a risk? Absolutely. But the only way to get a big reward is to take a big risk. I, for one, am pulling for you.

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  1. 1

    How does he get along with your children, Cheryl? As another mid-30s man on the fence about having kids, I think it’s important to consider that question. I loved the children of my last long term girlfriend. In fact, she was the one talking about maybe wanting another one, not me. Had other factors in that relationships changed, I would have been quite happy not having a child, and helping her raise her two children. Perhaps he might think similarly at some point.

  2. 2
    Karl R

    Cheryl said: (original post)
    “I had my children and didn’t want any more and he was ‘undecided’ as to whether he wanted any.”

    Under those circumstances, I always accepted the date. I was quite clear that I didn’t want kids. If an “undecided” woman chose to enter a long-term relationship with me, she was making a decision.

    Cheryl asked: (original post)
    “If someone offered you an amazing relationship for 3 years, but after that 3 years is up, it had to end, would you do it?”


    Of course, at the time I chose to pursue the relationship, it seemed unlikely to last anywhere close to 3 years. I figured a few months was more likely. (She explicitly told me she wasn’t interested in a serious relationship, and that I was too young for her.)

    Being in a great relationship (even if it wouldn’t last) didn’t interfere with any of my long-term goals. Since it was the best relationship I had in years, I couldn’t see any reason to end it.

    Our  relationship is now approaching the two-year mark, and it seems likely to last far longer than 3 years.

    Life holds no guarantees. But if you eliminate all of the possibilities which might not work, then you’ll eliminate all of your possibilities.

  3. 3

    To be clear: The issue is that he might want kids in the future and you’re 100% sure that you don’t want any more, so you are thinking to break up now rather than wait till the relationship enters crisis mode over the issue?

    It’s very hard to know how you’re going to feel about something years before it happens.

    Other possible scenarios to consider:

    1) You break up for a reason unrelated to the kids issue.

    2) You may decide that you do want another child after all, once that window starts to close.

    3) He may decide that he doesn’t need to have his own biological children and that being a stepdad is great.

    4) He may find that he can’t have his own biological children.

    5) He may find out that he already is a dad from a prior liaison and that now he is on the hook for child support.  

    6) You can break up three years from now when he decides to have kids with someone other than  you, and it might all be OK  when it happens.  

  4. 4

    This is a toughie but I can only offer advice I am following myself at the moment.   If you love him and feel that there is a chance this will work, give it a bit more time.   I fall in the following category  – “Interracial couples start intense relationships, hoping for their family blessings that never actually come.”
    I won’t   go into long and boring details but suffice to say that it is his family who will not accept the relationship.   We’ve discussed the situation to death and we’re dealing with it.   We are committed to each other, with or without their blessing.   I’m taking a chance and I acknowledge it but he is worth the risk and I trust him.   Coming back to the point of children, he has decided that he does not want children.   He says that there is a very slim possibility that he *may* change his mind later but he wants me to understand that at the moment, children are not in the cards for him and will most likely never be.   We had always bantered lightly about this from the beginning of the relationship, with him erring on the side of “no children” and with me always wanting to leave the possibility open but it was only after we had a serious talk recently that I realized how strongly he felt about it. He never really wanted children anyway but with the added issues that come with an interracial union, it has become an impossibility.   We’ve been together for a year now and the discussion was inevitable.   I went through 3 or 4 very rough days fighting with myself.   I do not particularly enjoy children and was never completely convinced that I wanted to have them.   I just assumed that it was something that would eventually happen because that is what people do: they get married and have children.   I am a person with many interests and I value my free time greatly so children would be a big sacrifice.   I have no great urge to pass on my genes through procreation either.   Then why did I panic when the choice of having children might suddenly not be a choice at all?   I’m not sure.   I haven’t completely answered that question myself yet.   I (probably along with half the human population) enjoy keeping my options open.   This potentially closed door hit me like a slap in the face and forced me to consider whether I really wanted to have children more than staying with my boyfriend or whether I just wanted the security of keeping that door open in case I felt like walking through it later.   I have come to the conclusion that it is the latter.   Some women just know that they are meant to raise little ones some day.   I am not one of those women.   Children are attractive because they would be something we would make together but even so, I’m not completely convinced that is a good enough reason to have them.   Without him, the children are meaningless.   So for now, I’m staying.   I am slowly reconciling myself to the idea of no children and trying to see if I can live with it.   I think I can.   In any case, the door is closed but not locked.   He will change and I will change over the course of the next few years.   I’m 29, old enough to have very strong opinions but still young enough to change a lot in the upcoming years.   He is 33 and has a few years on me but I would say that he is in the same boat.   In any case, we do know that we are crazy about each other and have found some unique combinations of qualities and personality traits that are special and difficult to find elsewhere. That is worth holding on to…

    Good luck to you and I hope you find your answer.  

  5. 5

    I see a pretty easy solution to this problem.   Evan has said time and again that the flush of infatuation wears off in about 18-24 months.   So why not enjoy this flush of infatuation for the 24 months, and then see how you feel?   He may not seem so perfect then, or he may be worth sacrificing for or he may have decided that you’re worth sacrificing for.

    In case you can’t reach a compromise after 24 months, maybe your hormones  won’t feel that you lost so great of a love, the pain might be a little less tortuous for you and for him.   In the meantime, enjoy what you have…

  6. 6

    I would take my chances, and stay in the relationship. You are sacrificing two of life’s greatest gifts ~ love, and the present, by trying to make a decision about a future that may very well never happen. And if he truly does decide that he wants his own biological children later on, then I would feel very blessed to have been able to spend a wonderful part of my life with this man, and I would feel grateful for having had the opportunity to experience something that some people never do. Your life will have been enriched for the better. It’s really all in our attitude.
    Who knows; maybe adoption would be a possibility, and as you grow deeper in your relationship with him, you may find that you’re the one who changes her mind. 🙂

  7. 7

    I was in this same situation, except I was  a woman in my  early 30’s who’s stance on kids was “I’m not sure if I want kids, but I would like to have the option”  and I was dating a man a decade older than me who’s stance was “I’ve never wanted kids in the past, I don’t want kids now.   I may want kids in the future, but who knows if I will?”   After almost two years of agonizing back and forth, counseling, baby decision workshops, I eventually broke it off with him.   The kids issue is a deal-breaker.   I think that, although everyone is responsible for making the decision to stay/go in a relationship for him/herself, this issue is a case where people should be respectful of the other’s side of the coin as well.

    In my opinion, you did the responsible thing by breaking it off with him.   As painful as it is now, you are both better off in the long run.   He should be with someone with whom he has the “option” to have kids, and you should be with someone who doesn’t want any.   Again, the kids issue is a one of the biggest “deal breaker” issues there is, if not the biggest.

    I still don’t have children, but know now that I want a family.   Walking away from my ex was the best thing I ever did and I would do it again in a heartbeat, despite all the pain.

  8. 8

    i am inclined to agree that, at least in this situation, cheryl was right to let this go. i don’t think its a good idea to stay in a relationship hoping the other person’s mind will change. if you are apart for awhile, and he decides he can’t be without you so he’s willing to let go of making new babies then that is one thing. or if cheryl decides she would have a baby then the relationship could progress. but staying together on the hope one of you will change your mind about such an important issue doesn’t make sense to me. love between two people can be wonderful but not everything can be fixed.

  9. 9

    I don’t think the option was “this great relationship or no relationship”. I think their was chemistry and they had a torrid affair. But I don’t see someone that young wanting to marry her.

    I can offer the perspective that dating only gets harder as you get older when you are a woman? Why? Because it is harder for us to find someone to marry for a lot of reasons. With online dating we compete with younger woman.

    I would say dump him and find “fertile ground” – someone whom you would marry who would feel the same – this is why we date – there are plenty of people who fall into that category the trick is to find one with chemistry. I never date anyone I wouldn’t marry – and a younger guy who is not sure about kids is not fertile ground for me. Chemistry does not equate to a good life partner.   PLUS I would never want to marry someone who wanted kids and I prevented that for him – I would feel guilty.   

    You could be happy you had 3 good years – but I would rather have that for life and not have to worry or feel old or feel like i am depriving him. If it was right you would not have these questions.   

  10. 10

    This doesn’t sound like simply a “torrid affair” to me, in that it took some time for the two of them to get together, and they were friends first. And half my friends are married to guys who are a few years younger, so i wouldn’t rule it out on that basis.

    As long as he is undecided about having kids and it’s still early on, why not give it more time? Maybe not 3 years, but at least a few more months. Cheryl does have children, and her guy might decide that step-parenting is fulfilling enough. Just because someone isn’t sure about every aspect of a relationship after 7 months, doesn’t automatically mean that the relationship is the wrong one.  

  11. 11

    Wow….this whole subject actually poured a bit of salt in a wound I thought was almost healed.     It’s a good thing though because now I can speak from real experience.  

    I think Evan’s advice is great.   I believe Cheryl that if you want to stay in the relationship and  “see” if he will change his mind is a possibility.    Just go into it with your eyes wide open…and your heart open not guarded and ready.   If you choose not to…then  just chalk it up as wisdom  saving you and leaving you open to find the right person that wants the same things out of life and can be a partner hopefully until death do you part.   Yeah cliche but that is what we are all after so I am not the only crazy romantic.   My vote   only from my own experience is to let it go as much as it hurts.

    My story told only to help others.    Keep in mind that I made mistakes as well, this is not totally one sided.   I met and fell in love  with a man 10 yrs older. Very handsome,  great job, secure,  and became my friend and love.   He had been married about 12 yrs before and raised the ex/ex wifes son who was 3 yrs old.   That went fine but the  child never wanted to take his last name and the real father was out of the picture from the start. I had a son.   My son when he met him was about  9-10 yrs old. We had a couple of dates on about the 3rd or 4th he confessed to me that he never wanted to date someone with a child. I said
    well this  has been fun but I guess this  is where I say it’s been nice knowing ya.   I started for the door.    He stopped me and I fell for the ” well, lets see how things go” speech.   If I had my eyes open I would have realized that it was just a plan to keep having sex with me.   I thought oh, he is really gonna give this a chance!  It will be fine he will like my son I know it.     Well 3  – 4 yrs goes by and nothing….is changing.   So   without giving him an ultimatum I said I  really want to be married for my sake and my sons….I am losing time…if you think that is where you would like to go great if not then I  must move on.   I was very open to honesty…this is his life too.   He chose to marry me.   Yep, you got it.   It didn’t turn out well.   He tried for about 3 1/2 yrs then gave me an ultimatum.   It was him or my son…one had to go.   My son was about  15-16 yrs old.      My son’s father was no father, never around, neither were the grandparents.   My son really wanted him to be his friend at least and maybe just maybe become a step dad.   My ex…never talked to my son barely would have a conversation with him.   He accused my son of horrible things….finally one night when he was so drunk he could barely stand and not letting me go up my own stairs…my son came down to see if I was ok…and the ex proceeded to say…”come on, what you gonna do you little punk ass bitch”   well……I told him to leave…and then tried  over the next few days to calm down and try to make this work out…some how.   But he said  for me to call my lawyer.   Yep…that is one way it could work out….so you can take the chance like did ….it might  work out like the Brady Bunch….just be ready for the ugly version.  Since you also wanted to try don’t solely blame them.   Be fair too.   Wishing you all the best Cheryl! xo

    PS… I am still unmarried….my son is almost 21 yrs old and a wonderful young man.              

  12. 12


    I’m so sorry that happened to you.   Unfortunately there are very selfish people – men and women alike – who don’t want a partner with children then decide to marry or be involved with the parent thinking they will get the parent to choose them over the child.   That is a sacred bond that is not to be messed with.     

  13. 13

    Carrie – wow!! That is so sad – I am sorry for you and what a selfish, heartless jerk – it is good that you shared this with us – it is a lesson and what a hard one for you – but you have your son that is more important than anything else. HUGS!!!!

    I think the right relationship should start right and just get better for everyone. It isn’t that hard – you just have to do your homework and DATE and date and be willing to stay single until the right person comes along.   Some people have a stronger stomach than me and they can take a chance. I want something that feels right from the start for both. I am older – i have my child and am very happy. Dating and a relationship is icing on the cake stuff – happy yet sweet.  

  14. 14

    I think if this man has not made children by now, he never will.

  15. 15

    After reading Carrie’s heartbreaking story (and Carrie, as a mother myself, I am sorry for what you went through), I wonder if Cheryl’s guy has spent any time around her children, or if he’s expressed anything to her about them, like a desire to spend family time together. The more I think about this one, the more I am starting to change my mind from my original post because when it comes to children, like blended families, there are often lots of obstacles, such as a parent favoring their biological child over their step-children, or as in Carrie’s case, a jealous parent who resents his wife’s loving and protective son.
    I also re-read the letter and realized that while she’s having a dilemma, she’s not exactly sure how she feels about the guy, so breaking up at this point in time may not result in losing all that much. I did notice that neither of them mentioned they hoped to get married someday. Sharing your life with someone doesn’t automatically equate with marriage. The guy could be sitting on the fence because he’s not sure he’d want to marry Cheryl or if he even wants to be married to anyone, but fears mentioning this. Without more info., I can’t decide on this one.

  16. 16

    While I’m sorry for what Carrie went through, I don’t think her situation is the same as Cheryl’s. Carrie’s boyfriend told her very early on that he never wanted to date someone with a child. Not much of a gray area there. That is not the same as Cheryl’s boyfriend being uncertain about wanting biological kids.

  17. 17

    The problem with men who are “uncertain” about having kids is that they can rtemain uncertain for a very long time. This man clearly wants to keep his options open on that front   because, well…. they ARE open, as far as he’s concerned. Men can father children at any point in their lives and see no need to take a definate decision on the matter. I have met men of 50 who still don’t rule out the idea that they might like to father a child. So the issue for Cheryl is that if she wants an answer yes or no she may well not get one for a very long time.
    I dated a man when I was in my early 40s who was in his early 30s and thought he wanted children “someday, but not now”. I don’t have kids, didn’t desperately want kids, and was getting too old to have them anyway. And since he thought he wanted to do this “in the future” but definately didn’t want it now, by the time he was ready I’d be too old.Because the relationship was otherwise wonderful, I decided to take a chance and  spent 2 years with him, hoping he’d choose me and our relationship over an unborn foetus he’d never met. He didn’t. I eventually had to break up with him because he would never fully commit to me and our life together because of his ideas about having kids at some point. The thing is, he was PERFECTLY HAPPY to go  along in our relationship for as long as he could persuade me to continue in it, because he was enjoying it and the kids thing wasn’t a pressing issue at that point as far as he was concerned. In the end, I wasted 2 years of my life (plus another year getting over him) on a man who wouldn’t ever  fully commit. Now I’m back dating, and 3 years older. Not a good outcome. Men do what suits them at the time.  I took his strong interest in the relationship to indicate a possible future, but for him it didn’t. He was just along for the ride.  

  18. 18

    The more time you spend with the wrong man is time you lost finding the right one. He has stated clearly that he’s undecided about children and as helene said, may remain uncertain for years and years.

    If Cheryl wants to spend her life with someone and not just the next 3-5 yrs. with someone temporary, only to  begin dating again at 50,  she should find someone  certain about large life decisions such as this.  

  19. 19

    @17: I’s something of a myth that men can reproduce for all of their lives–there’s a lot that’s been written of late on the studies that show this isn’t the case. And even if he can, or believes he can, a 50-year-old guy is going to have a really hard time finding that much-younger gal to go along with him  since she knows what her  options are. (Who has having kids at 50 as a life plan anyway? Shudder…)

    Sounds like a lame excuse to get out, if  you ask me. Better off without him…

  20. 20

    To answer a few questions…

    We both want to be married someday.   Our relationship had not evolved enough for me to be certain he is the one.   He had in no way disqualified himself yet.   It is not a “torrid affair.”   We talked for 3 months before I met him.   We have been dating for 14 months, the last 9 of which were exclusive.   He did not date anyone else, but I did. He has met my children, but has only had limited involvement with them.

    He wants to remain friends, and I have asked him for time alone to make some decisions.   He is giving me this.  

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