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How To Have Difficult Dating Conversations


I am often accused of thinking like a man. I wasn’t aware that men thought. (I kid) I certainly would never want to think like one. I can only assume my lack of proper emotional reactions, to typical situations, warrants such outrageous charges.

One such time being when I was naked in bed with a man, presumably about to have sex, when he asked me the absolute worst thing that you can ever ask a person who is naked in your bed. “Where do you see the relationship going?” I must have given the wrong answer because we didn’t have sex. In fact that was the last time until very recently that we ever spoke and certainly the last time I was in his bed.

The lesson I learned, despite having tried to avoid these tough questions and difficult conversations is; they are unavoidable. If you refuse to have them, it’s likely that you will not have a relationship. If you’re a woman who chooses not to be the one to ask cliché relationship questions like ‘where do you see this going’? The man will either ask you or stop calling you. And if you give the wrong answer apparently both.

My answer was that I didn’t know because I didn’t know. Initially I had liked this guy a lot but overtime I’d begun to have serious doubts to our compatibility. He began to notice my painfully obvious mixed signals, declining invitations, not answering his calls and not calling when I said I would. So his inquiry was perfectly appropriate just not his timing.

So how and when should you have these difficult conversations? When is the right time to ask the tough questions and who should be the one to ask them? Honestly, I don’t know. I was hoping someone could tell me. I don’t have a fear of intimacy; I have a fear of talking about commitment. Had I told this man that I wanted to be his girlfriend maybe we would have had sex but I didn’t know if I wanted to be his girlfriend. If he’d asked me straight out, I most likely would’ve lied. Or I would’ve been certain that whatever my answer might have been it would prove to be a lie once I got dressed.

A better question, or at least a more telling one would have been, “If I’m interested in being serious how would you feel about that?” or possibly, “Do you want to be in a relationship with me?”
That’s the best that I can come up with, relationship expert I am not. You have to hope that you’re not dealing with someone like me who is likely to lie. Not blatantly to your face but will give you an answer with an expiration date, bullsh*t you. I can’t remember a time when a man asked me a serious relationship question and I gave an answer that wasn’t completely full of sh*t. Maybe that’s why I am not in a relationship.

A cardinal rule in effective communication is to never ask a question when you need to make a statement. When you know how you feel it might be the best idea just to share with whoever you’re dating. Is this any more difficult than asking what the other person feels and risking them lying to you?

I’ve spent a large part of my single life dodging these very tough questions and statements. Once you broach the subject if the response isn’t the right one, courtships are likely to end. Maybe they should. Why waste time with someone who has no desire to be in a relationship with you? To be honest, you shouldn’t. Your choices then are for things to end when you know they will or to end to your surprise and possible dismay.

Either way, the threat of things ending is what we as single people fear most. Having to start again with someone new and no guarantee that a relationship will bloom, sucks. It’s the reason that many single men and women hate dating; it takes too many tries. Facing the fact that we might be rejected or have to do the rejecting and thus be “the bad guy” also sucks. Once you talk about a relationship if you’re the one to back out of the deal then essentially you are an insensitive asshole, sorry to say.

It’s a sick game of would you rather? Would you rather ask the question or give the wrong answer? Would you rather be hated or heart-broken? There is no mastering the art of avoidance. Either the tough talks will be had or you’re on the fast track to ending whatever it is that you have with this person. (That you can’t seem to talk about) I wish I could tell you how to make it easy. In my estimation there is no solution other than to show some guts, even if it happens in bed.

My best friend said it best, of my embarrassment and brutal rejection, “If you’re going to dump me, at least have the decency to sleep with me.” Especially if my clothes are already off.

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