Five Ways to Know When To Leave Your Lover


It isn’t rocket science. It isn’t even behavioral science. It’s just common sense. Here are five criteria you can use to evaluate the staying power of your relationship. If all five aren’t met, cue up Paul Simon’s “Fifty Ways to Leave your Lover.”

1. Is she crazy about you? If your lover isn’t spontaneously doing things that display a loss of objectivity where you’re concerned, start practicing your breakup speech. There are two key words that should answer this question. Spontaneity and hyperbole. If everything he says about you and does for you is not completely over the top, such as, telling you how gorgeous you are when you’ve just gotten out of bed, or making sure you overhear him bragging about you to others, he isn’t really crazy about you. If she doesn’t surprise you with small gifts and precious gestures, just because it’s Tuesday, just because you’re you, or write you poetry, or take a hundred photos of you because you look so perfect in that rare fluorescent light, she’s probably not all in.

2. Does he respect you? Respect comes in various forms. One of them is boundaries. Does he take your stuff without asking, assuming that what’s yours is his? Does he treat you as an equal? Does he really listen when you talk? Does she value your dreams and problems as much as her own? Does she keep your secrets? Does he keep secrets from you? Does she try to manipulate you? Has he been physically aggressive with you? All of these questions are rooted in respect. If there isn’t any, or isn’t enough, it’s time to say, “It’s not me, it’s you.”

3. Is she emotionally, spiritually and psychologically healthy? Yes, you want your lover to be crazy about you, but not mentally ill. And keep in mind that mental illness is on a continuum. Just because someone is able to function outside of an institution, even keep a job, even make a lot of money or have professional success, doesn’t mean he is healthy enough to be in a relationship. If your partner’s emotional responses are disproportionate to the stimuli, that’s a big red flag, regardless of whether it is too much or too little, You want someone who cares about themselves, values themselves, is self-confident, and independent, but if that is taken to too great an extreme, it’s time to revise your profile on If you get the impression that he really needs you, so much that he really can’t live without you, start planning your exit route. Remember, love is setting one free to see if she comes back to you, not vampish leeching. Despite what a lot of love songs say, “I need you,” is a warning, not a comfort. If she has to be the center of your world, your thoughts, and your consciousness every second of every day and it still isn’t enough, don’t take time to send a breakup text. Don’t go back for your toothbrush and the extra pair of underwear. Change your number, your email, and research the process for obtaining a restraining order in your jurisdiction.

4. Is he your intellectual peer? If he isn’t, you’ll know right away. It doesn’t matter what he looks like or how physically attractive he may be. It doesn’t matter how much he needs your help or appreciates the way you broaden his world, if he isn’t your intellectual peer, it will end badly. It may take ten or twenty years, or twenty weeks, but it will end badly. Cut your losses. The same is true if you’re the one with the lesser IQ. If the gap is very wide, you’ll never get the respect you deserve. If she stays with you, she will want to dominate you. So that’s two strikes, not just one.

5. Does she get you? This is also something you’ll know right away. So here’s a quick test. Before you invest a whole evening with this person, tell her the weirdest or quirkiest thing about you. You’ll know from the reaction whether you’ve struck fire, or it’s a burnout. If you have any doubts, you can assume it’s the latter.

This is the advice I’ve given my two Gen Y daughters. To my surprise, they’ve both followed it, and both are doing very well in their relationships. It isn’t a coincidence, and trust me. There are no exceptions. It is a straight flush or nothing. One strike and he’s out. Period. You’ll thank me later.

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