Dating Daringly

I’ve been talking to a lot of friends about dating recently. So much so that I worry that they will get sick of me asking about it or bringing it up… (If that is the case, I apologize. Too, let me know and I will try to find other topics of discussion.)

But dating has weighed on my mind for awhile now. I think that is a very appropriate word: weigh. Sometimes being single and dating feels like a weight. (Not always…)

In talking with my friends, I’ve discovered I’m not alone in this sort of feeling. The most positive adjective I’ve heard describing dating lately was “awkward.” Not exactly a lightning bolts and birds singing sort of word… Annoyed

Others include: frustrating, a waste of time, self esteem crushing, suck-y…

And this isn’t just from the ladies. My gentlemen friends use the same sorts of words.

So how can we come together and get what we want? Both sides seem to want honesty, compassion, connection, respect… If both men and women want these things, why are they often missing from the dating world? (Specifically heteronormative dating, though I’m guessing many of these same trends exist in the LGBT community. I want to be clear that I completely support the LGBT community, but since I’m not a part of it I want to be mindful that I am representing a specific facet of the dating world.)

I recently met with a friend, and of course dating came up. I was expressing some of my frustrations, which I go into a bit more detail here. She said that something that helps her through those frustrating times is that she keeps in mind that she dates the way she wants to be dated. She presents her authentic self, and all she can hope is that she’ll meet people who will do the same. Even if the relationship falls through, she knows that she did what she could do and should do to have a healthy relationship if it was meant to me.

I think that is the answer to both sides getting what they want. We need to be our authentic selves while dating, even in the early stages. If we are people who honor honesty, compassion, connection, and respect in our regular lives, we don’t stop those things while dating.

I recently dated a man who just stopped calling. We went on six-ish very nice dates, and soon after date six he dropped off the face of the planet. One of those “I’ll call you” sorts of scenarios. I have no idea what happened. And it occurred to me that if I asked his friends to describe him, they would describe him favorably. “Good guy,” “loyal,” “fun,” “honest,” “hard worker,” “respectful,” “caring,” etc… In fact if I asked him to describe himself, he might use many of those same words. They would say all of those things, and they would all be true! So how could a man with all of those positive attributes treat me so disrespectfully and so carelessly?


I don’t exactly know the answer, but I think that he doesn’t think what he did was “bad.” He thinks that he is honest and respectful, and him not calling a woman he dated only briefly does not violate those traits. It’s just what you do when you don’t want to see someone anymore. You just stop texting/calling, even if you told them you would. It’s not a lie to not call when you said you would. It’s not disrespectful to ignore someone you’ve only seen six times. No biggie…

But it is a big deal, and it hurts.

The good thing is that we can do something about it! We can date the way we want to be dated.

When we don’t want to see someone who expresses a continued interest in us, we don’t just ignore their texts or calls. Instead, we reach out to them and tell them that we aren’t a match, but thank you for an interesting time.

Or if we like someone, but a conversation during an early date gets awkward, we don’t just stop all communication. We check in with the person and see if we can figure out why things felt awkward.

I strongly feel that doing these little, uncomfortable things will leave everyone feeling better in the long run. I felt woefully guilty about calling things off with a man I went on two dates with. I liked him, but I felt strongly that I didn’t want a romantic relationship with him. I’m glad I was honest with him, because we’ve remained friends. I straight up bawled my eyes out “breaking up” with a guy I dated for a week, because I felt so guilty about calling things off. I certainly didn’t want to hurt his feelings, and I know I handled certain aspects of that brief relationship poorly. At the same time I knew that I didn’t want to see him any more. We didn’t remain in contact, but I’m still glad I gave him and myself closure. Every time I’ve had to tell a guy I’m not interested has felt incredibly uncomfortable. Yet I’m so glad I’ve done it, because I’ve rarely had men extend me that courtesy. And that feels worse by far. (I don’t want to imply that only men do this. It sounds like it goes both ways from talking to my guy friends.)

On the opposite side of things, I messaged the guy I recently dated (Mr. I’ll-call-you) once I was 95% sure I was actually being blown off. In that message I let him know I was sad and disappointed that our brief relationship was ending that way. I told him that I had a great deal of fun with him, and I had a strong impression that he enjoyed my company too. I told him that I wished he had contacted me to let me know he was no longer romantically interested in me, because if he had there was the potential for us to remain friends. With contact just ending, that wasn’t really an option anymore. I got no response back, but I’m glad that I let him know how I feel. More, I’m glad I let him know how I feel in a positive sort of way (i.e. not cussing him out and blaming him). Maybe, just maybe, he’ll end things better with the next woman he dates.

I can hope that by being my true self while dating, whether dumpee or dumper (or can I timidly say girlfriend?), that perhaps those people that I interact with will take something positive away from their experience with me. Perhaps the best way to think of it is paying it forward. We’ve been hurt. We’ve had our hearts broken. But it doesn’t do any good to keep passing that heartbreak on to others. We can feel it, and we can be honest about our hurt. But we can pay forward the honesty, compassion, connection, and respect that we want and deserve. We can pay it forward even if the relationship needs to end. I guess that’s what I call ‘dating daringly.’

So for all of you single folks, go forth and date daringly! And may the odds be ever in your favor.

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