Dear Red: How do I Break Up with Someone I Like?

Dear Red,

I have been dating two different women at the same time. I didn't plan it that way. One I was genuinely interested in and pursued for a time, the other just kind of forced herself on me. They are both wonderful people and both have qualities I admire and look for in women. However, for whatever reason, I just don't feel a "click" with either of them.

My question is; how do you stop dating someone who doesn't really have anything overtly wrong with them, but you don't feel a real connection with, without being a dick? I've heard everything from "give it a chance" to "stop talking to them completely." I adon't want to be an asshole, as they are both genuinely nice.

So, should I just swallow my niceness and tell them to bugger off? What do I do?


Trying to be a Nice Guy

Dear Trying to be a Nice Guy,

Hmmm, interesting question, and I don't know if there's REALLY a good way to tell an otherwise awesome person that it's just not working.

(You may notice I'm not berating you for dating more than one woman at a time. I don't know your arrangements with them or, I've done the dating multiple people at a time myself, know. :))

I guess what seems to work for me is the phrase, "friendship vibe."

(Uhh...not that I have to use it that often. You know, on account of not having dates and shit.)

Anyway, it's a tricky phrase, to be sure, because you have to check in and make sure that you do indeed want to be friends with the person you're about to deliver the line to.

For example, I have found that it's a phrase I've used when I actually meant, "I'd pretty much prefer to never see you again." And then I ended up hurting someone's feelings when I haven't responded to "friendly" texts or whatever (that they were sending because I said I wanted to be friends).

I've also found that it can give false hope to someone who thinks that maybe my "friendship vibe" with eventually turn into a "boning vibe."

But really, at the end of the day, it pays to be honest. I can tell you that it's always been easier for me to hear from someone, "I think you're cool, but I don't feel that way toward you," than for someone to string me along endlessly (whether he means to or not). When I hear from someone--in a relatively kind way--that they don't view me as girlfriend material, it gives me the choice to cut my own emotional ties and move on.

So yeah, I guess all that to say, be as honest as you can while being as kind as you can.

It may sting to hear that someone is just not that into you, but it's way, WAY worse (unkind, even) to find out later that he/she stayed with you just because you were the only thing around. Or that you were nice, but not nice enough to want to be with long term.

Ouch, right?

Seriously, I'm sure you'll find a way to work it so you're not an asshole. And if they're both as awesome as you say, they should take it pretty well.

Good luck!



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