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

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.

Ready for Lasting Love?
Ready for Lasting Love?

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.