Is the Dating Grass Greener on the Other Side?

OK, show of hands, who is sick and tired of seeing everyone else living their “happily ever after” while you go on shitty date after shitty date? I get it, it’s extremely frustrating. As happy and fulfilled as your single life may be, you still want your own “happily ever after” whatever that looks like for you. Getting a divorce or ending any type of long term relationship puts that front and center. You thought you had your “happily ever after”, then, BAM!, it’s gone, just like that.  You’re thrown back into the dating game, back into abyss we call single.  A tad dramatic, ha ha, well, maybe, but it begs the question, is the dating grass greener on the other side? Well, it’s all about perspective.

dating-grass-greenerIs the Dating Grass Greener on the Other Side?

Last week I listened to an interview with the author of Missing Out: In Praise of the Unlived Life. The main premise of the book is that each and every one of us have two lives – our actual life and the one that we wish for. This “unlived life”, according to the author, can occupy a large part of our mental life. Interestingly enough, he goes on to say that the people we have failed to be and the road not taken preoccupies our minds.  Essentially, the life that got away never really goes away. This really resonated with me, particularly in terms of dating and my own life.

So, you feel like your life is one big consolation prize? You’re not alone. Everyone is in the same boat … it might be in regards to dating or it might be for something else, but we’ve all got some sort of regret in life. People are so preoccupied by the life they are not leading that it makes them miserable. People end up spending so much time in the “dream” that they forget to live. You can’t live in the “if only” world. We tend to do that a lot when we’re single and dating.

We live in a culture that gives the impression of endless possibilities. This theme was also discussed by Psychologist Barry Schwartz in his Paradox of Choice discussions. He said that we have too many choices and we don’t know what to choose. All these choices have the potential to allow us to do better but actually make us feel worse because our expectations increase which in turn produces less satisfaction with whatever results we get. He said that, frankly, the real secret to happiness is low expectations. It is often thought that Social Media is perpetuating this “missing out phenomenon” and makes people feel left out where they should be thinking “what else can I be doing with my time that’s more productive”.

The Grass is Greener Where You Water It

What is the solution? The solution is to live your life. Yes, simple as that. Life should be “what do I make with the experience I have had” not “what might have been”.  Regret is part of life and it’s part of reality. Regret reminds us that we can do better. It’s about the lessons learned and improving ourselves. Part of living is bearing disappointment. What’s wrong with that? Well, no one wants to feel pain or suffering. No one wants to wonder “what if”. The grass isn’t greener on the other side, it’s greener where you water it! This applies to ALL aspects of your life, even dating. You get what you give. You have to stop comparing yourself to what others have. You need to stop dwelling on your “unlived life”.  You also need to stop living in the past. We need to live our lives as they are. We should be grateful for what we do have and not focus on what’s missing. Remember that dating is a process … you need to enjoy this process. Live in the present and you’ll definitely be MUCH happier.

Do you agree with the author? Do you think we spend too much time in the “what if” world that we lose sight of reality? Is the grass REALLY greener on the other side? I would love your thoughts in the comments!

Your Sister in Dating Bliss,

Single Dating Diva

Copyright Single Dating Diva


  1. This is one area where I’ve changed. Now I am genuinely happy when I see a couple that are really into each other. However sometimes I think “well they are both young and hot, so that figures doesn’t it?”

    One of the reasons I quit Facebook was too often witnessing other people’s relationships go through difficulties and implode. I found that very depressing.


    • Oh ya I agree … Facebook is an endless pit of things to make you depressed … whether it’s the “happy couple” who wants to tell you how happy they are every chance they get, or people’s rise and falls. It’s exhausting! Thanks so much for the comment!


  2. I’ve realized that the grass is always greener no matter what. If I’m single, I wish I were in a relationship. Then when I am in the relationship, I wish I were single. We have to realize that no matter where you are, there is always issues to face. Want to be rich? Well now you have to deal with paying higher taxes, having friends and family members hit you up for money, etc. Like you said, enjoy your life and live it to it’s fullest. Enjoy what you have.


    • Thanks Don. I agree, no one is ever truly happy with what they have. There’s always something more ideal or appealing on “the other side”. It’s only by accepting what you have, and being grateful for it, that you will truly be happy.


  3. Absolutely yes! The grass is greener where you water it. Period. So many couples come to me on the brink of divorce and they don’t think they can make it work because there’s been so much hurt and pain. Wouldn’t you know it, they haven’t done anything to water their relationship for years. Instead of stepping out, water the relationship you have. Most people are pleasantly surprised how well it works.


  4. Well – without listening to the interview or reading the book, I’d have to say I somewhat agree and somewhat disagree. We all have things we want and are actively pursuing for ourselves – whether it be career, lifestyle, whatever. The problem is, we can’t get into that mindset for relationships… even tho we think we want to be coupled up. We have to learn to be content exactly where we are, and strike a balance of continuing to pursue and achieve our life goals. Tough tap dance, but very rewarding when we let the pursuit of a relationship go, and work on ourselves and what makes us happy as a single first. Just my two bucks worth.


    • Thanks Ms. Cheevious. Yes, you’re right, you still need your goals and aspirations, but I think the author was saying we shouldn’t “live” there. Live in the present and be content where you are, but still strive for better. Thanks for the two bucks!!


  5. This is great! Very inspirational, too! People do need to focus on the here and now instead of “what if” or “what would have.” I love this!


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