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When do you decide to stop dating someone?

Dating involves extending yourself to people you don’t know, and that requires taking risks. Inevitably some dates are better than others – and sometimes people who are interested in you aren’t interesting to you.  Eliminating someone from your dating pool is unpleasant; it’s also unavoidable.  I think some men avoid getting into the dating game because they worry they wouldn’t know how to end something that isn’t working for them.

Some people waste a lot of time and emotional energy because they are unwilling to express the unpleasant truth. They continue to go out with someone even after they are certain that it just isn’t going to happen because they can’t bring themselves to let the other person down. Or they take the spineless way out and just stop returning phone calls, hoping the pursuer will get the hint or get tired of getting voicemail.

There are many reasons for not taking either of these approaches. For one thing, they draw the process out for weeks and leave the person getting let down wondering what happened or feeling you’ve not been honest.

They are much more likely to be pissed off. And face it – you’re not going to feel good about yourself if you know you’re being less than candid with someone and not speaking the truth.  It’s no fun to hear “no,” and the guy you’ve been out with may very well be disappointed – although it happens to all of us, and we all get over it eventually. It isn’t easy to disappoint someone, so we avoid it.

So how do you tell someone you’re not interested while not being more hurtful than necessary? Saying goodbye isn’t pleasant, but you can do things that make it a bit easier.  Consider where you will talk – a neutral spot is likely to be easier.  (Thinking about doing a “virtual breakup” via email or text message?  That’s the easy way now, but you’ll regret it.  Be a man and talk to him.)  Think through what you want to say beforehand.  You may want to travel to your goodbye spot separately unless you are sure driving him home afterwards won’t be awkward.  As long as you don’t have a concern about his potential for getting physically aggressive, choose a place that’s private enough for sad feelings to be expressed or tears to flow without becoming a public spectacle.

Give yourself enough time to complete what you need to say.  Don’t offer false hope for the future if you are certain that’s not what you really want.  On the other hand, don’t be more hurtful than necessary.

Take responsibility. Keep the focus on yourself, not on him. (Psychotherapists call these “I statements.”) “Joe, I need to let you know that I’m just not feeling any chemistry here and I don’t want to waste your time” is much better than “You just don’t do it for me.” Avoid clichés like “It’s not you, it’s me;” that can feel like bad dialog from a chick flick.

Be kind. Saying “I appreciate the nice dinner last week” (or whatever) is an acknowledgement of the way he extended himself toward you. “You deserve someone who can give you something I’m just not able to” is both kind and a statement about your own feelings. It’s OK to say you’re sorry, especially if you know your decision is going to be hard for him to hear.  Do not, however, offer opinions like “Someday you’ll thank me for this because you’ll find someone wonderful.”  That certainly doesn’t speak to his reality right now.

Be clear. If your goal is to close the door, don’t leave it cracked open; you’ll just have to do this again. “I’m just not feeling a romantic connection with you” is much clearer than “I’m just not sure this is going to work out” if your goal is to end a conversation rather than begin one.

Friendship is a commitment, not a consolation prize. It’s dumb to say, “Let’s be friends instead” if you really don’t mean it and don’t want to see the guy again. And recognize that it is his right to decide whether he can be a friend with you after you’ve said a romantic relationship isn’t in the cards. It just might not be what he wants.

Even if no one wants to be told that their affection isn’t being returned, no one would prefer being strung along instead. And someone once told me, “The space for what you want in your life is occupied by what you’ve settled for.” Calling it off with someone when there is no future opens up a space for each of you to meet someone who can better suit you.

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