Recently, a good friend of mine asked me following: 
How do you know when it’s time to let go of a long-term relationship? 
She’s been with her guy on and off for a number of years. They’ve been through a lot; vast physical separation, infidelity, in between loves, times of extreme joy and times of equally extreme pain. Through it all they’ve managed to spend the last two years in relative peace. No states or countries separating them, no other men or women distracting them and, having both moved to a city far from their hometown, no family or friends to fall back on–for the first time in their relationship, it’s just them, and they have all the time in the world to just be. But in what should be the most wonderful time in their entire relationship, she cannot reconcile their seemingly miraculous survival of past tumultuousness against this unshakeable sense of unhappiness and dissatisfaction she now feels. And that is where her question was born.

So again, how do you know when it’s time to let go? 
I think there are a few questions we all should ask ourselves when we find ourselves at a crossroads in our relationship:

1. Am I Happy? — One should never enter a relationship out of loneliness or unhappiness, so assuming the best case scenario that you were relatively happy and content with your life before the relationship, how you answer the question “Am I happy”, is usually a good indicator of the effect the relationship is having on your life. Those who know you the best, whose opinions you trust, constantly telling you things like “you don’t seem like yourself”, or always asking you “is everything alright” are tell-tale signs of person negatively changed by a relationship.

2. In what ways have I grown since we’ve been together?  — The best relationships are those that challenge you to be better then you already are. This doesn’t mean you got cheated on multiple times and are now able to stand infidelity with ease. It’s more like… do you feel like your knowledge base has grown, have you acquired new tastes, are you able to trust the opposite sex more or less now, have they pushed you to excel in your career, do you feel spiritually challenged? All those are examples of ways in which a person grows when they’re in a healthy and productive relationship. Likewise, ask yourself; in what ways has your partner grown since you’ve been together? It goes both ways. It may not be that one of you isn’t putting their all into the relationship; the relationship may have just hit a dead end.

3. Are we intimate with one another? — Intimacy is an extremely important part of any relationship as the intimacy goes so goes the relationship. There are different types of intimacy:  There’s the physical- love making, and then there’s the emotional. The physical is too confusing to use as an indicator - especially in long-term relationships. Two people who’ve been together for while can have the greatest sex without ever making love to one another - without ever being truly intimate - physically. Gauging your emotional intimacy, however, can be very telling of what remains of your connection with your partner. Think about that thing, that idea that keeps you up at night, the thing that has always sat straddling your dreams and your reality. Maybe you work a corporate job but have always dreamed of opening your own business. Or maybe you secretly want to skip the annual Caribbean vacation and drive across country. Whatever it is, do you share that with your partner? Do you feel comfortable letting them into the deepest corners of your being? And likewise, do they share those things with you? Does there seem to be a vast expanse separating those things you each individually contemplate or desire and those things you actually discuss? All these are indicative of your level of emotional intimacy.

4. Have I let go of my anger over past wrongdoings? –This one is simple. Have you forgiven? If you’ve been seriously wronged, but decided to stick it out, have to let go of that anger. Does it still way heavily on your trust, your decision making (as it relates to the relationship) - if it does, then it will be nearly impossible for your relationship to progress.  

5. Do I see this person standing next to me in my most ideal future? –This is a tough one. When thinking about your life 10, 15 years from now, do you want it to be that person that’s there standing next to you. In unlocking the answer to that question, you are able to unlock your most sincere feelings about the relationship. If the answer is a resounding “yes… yes… yes!” then you know you have something worth fighting for. If the answer is no, then you have a tough decision in front of you.  Every minute you spend with someone who isn’t the person of your dreams is a moment you’re not spending with the person who is. The moments add to hours, those hours to days, days to weeks, weeks to months, and months to years.  And while those years may be filled with some really fun times, if you know that ultimately, this isn’t the life partner, then you’re just wasting time.

The above are just a few of the many questions one should consider when reaching a crossroad similar to the one my friend reached. When you’re at that point, honest reflection on your desires and where you are in the relationship is imperative. You may realize that you still love and care for the person, but that love just isn’t enough anymore. There’s nothing wrong with that; it’s only wrong when you do nothing about it.  It’s easy to paint the picture of our relationships with broad strokes -– characterizing them with clichés like “we’ve made it through the storm”, but what about what’s left on the other side of that storm.  What do you do if after making it through the storm you find not the brightly burning sun of spring, but a perpetually dull and lukewarm gray of an endless winter’s end?  If I had to sum up, in one sentence, my answer to my friends question it would be this: You know it’s time to let go when the memories of what you once had seem brighter and more wonderful than your present and future will ever be.