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Dear Wendy: “What’s The Kindest Way To Break Up With Six Men?”

Wendy is on vacation, so we’ll be posting some of her more popular past Dear Wendy columns (that some of you may have missed!) to get you through the week.

I’ve recently started dating in a normal, orderly way like other people date; formerly, I have only had long-term relationships which just sort of happened, no dates required. I’ve gone on dates with many men, with the goal of getting to know each of them before I choose to make a more serious commitment to any particular one. The problem is that they all seem to be really, really into me. As in, they want to bring me home to meet their parents. They call me pet names, they call me every day, my ears get sore from staying on the phone all night. They wonder what our babies would look like. It’s too much. And, just for the reference, these are all men I have known for less than one month, some I have not even kissed.


I have, happily, found that I’m more “into” one of the guys than the others, so it’s time for me to cut a few of them loose. The reason I am writing is because I am terribly, terribly bad at breaking up with people. Even if I’m not even technically in a relationship, I am bad at dishing out rejection. I am nice to a fault. What’s worse is I now have to do it six times! Yes, that’s right, six. I got a little in over my head! I know that the longer I delay the inevitable, the worse it is going to be. I am tempted to just fade out on them, but that’s kind of heartless. I hate to see people let down, and there’s no way to do this without inflicting some pain. It fills me with dread and keeps me awake at night. Since I’m going to have to do this, what would help me infinitely would be a script that I could follow. Can you help? — Too Nice For My Own Good

The short answer here is to tell each of the six men you want to “break up” with that you’ve enjoyed getting to know them, but you’ve recently started dating someone you really click with and you’ve decided to become exclusive with him. Then tell them you’ve enjoyed their company and you wish them well. Since you’ve been going out with each of these men less than a month, and haven’t even kissed some of them, I’d say this is the most you owe and you can deliver the message in an email. Hit “send” and be done with it. If they reply with anything other than well wishes for you, ignore them. You do not need to tolerate name-calling, character-bashing, or questions about your decision. None of these men are boyfriends; you have not formed real relationships with any of them, and you don’t owe any more information than what you’ve given: a reason that’s as straightforward as they come.

What concerns me, TNFMOG, is that you seem to truly believe a rejection from you is going to tear these men apart. I don’t know if that speaks to an inherent sense of narcissism on your part, an unusual amount of sympathy, or a similar experience in your own past that left you emotionally worse-for-wear, but the truth is: these guys are going to be just fine. And if they aren’t? Well, that says more about their overall mental stability than some hold you might think you have on them. If you’ve been balancing six men — seven, if you count the one you’ve decided to become serious with — for less than a month, I can’t imagine you’ve had time to invest much in each one or to form very meaningful bonds with any of them.

What I imagine is happening here is that you attract a very needy type of man. Your all-inclusive dating style means you’ve probably let men into your life who are often over-looked by others. It makes sense, then, that they’d instantly latch onto the one woman who’s given them a shot, particularly if you’re pretty and have other nice qualities. If you genuinely thought all six of these men had boyfriend potential, then more power to you for getting to know them and testing that potential. But if you went out with even one of them because you were “too nice” to reject him from the get-go, that’s actually crueler than giving him a firm “no” before leading him on for several weeks.

I do genuinely wish you well with the man you’ve decided to become exclusive with, but if things don’t work out between you and you find yourself back on the market, I urge you to be more discerning in choosing a date. You do not have to go out with every man who asks you. If you’re not attracted or interested in the guy and don’t see any boyfriend potential there for you, saying “no” sooner rather than later is so much easier — and kinder — on you both.

*Do you have a relationship/dating question I can help with? Send me your letters at dearwendy@thefrisky.com.

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