optimism and dating disappointment

Don’t let the douchebags get you down: optimism in dating

Expectation management: it’s a thing. Having no or low expectations means they are more likely to be exceeded. Hope is the enemy of expectation management. But what is better? Regular dating disappointment with occasional glimmers of excitement, or never having the pain?

In investing, we talk about risk-reward. High-risk investments are those more likely to provide higher gains. But they could also wipe out your savings. Conversely, advisors will tell you the earlier you can get in the market the better, even with small amounts and low-risk investment vehicles.

Given my experiences this year, I’ve been thinking about the number of dating disasters I’ve had. It occurred to me it could have more to do with the volume of men I’ve met, than consistent bad choices or inherent bad luck. In other words, if I’ve met one hundred men and had twenty crap experiences, it’s not a worse track record than someone who meets ten and has only two to speak of.

Is it worse to have twenty bad experiences than two? Of course. At times, it’s difficult to not let it get me down. To have had several men who don’t see my worth, or don’t want me when I want them? Yeah, hard to not internalize that. When I value someone highly and see potential and they don’t? When they are the ones I’m told who I should pursue, the ones who I feel are closer to my equals, yet they don’t pursue me back? I’m gutted.

So I’ve had to build my dating resiliency. It’s so easy to let men undermine my self-worth. So easy to tell myself I’m somehow broken or wrong about what I have to offer. There can be ten men who would love to date me, but if the next one I want doesn’t want me back, it’s hard to remember those ten. It really only matters when it’s the ones you want.

I’m not a natural self-promoter. I know there are things I’m good at (you’ll rarely hear me say I’m exceptional at anything) but try to get me to talk about it and I’m very uncomfortable. Dating has in some ways forced me to be bolder about this. In fighting to maintain my self-worth through this process, I have to remind myself who and what I am. This blog and my Instagram account have given me a window into how I’m seen through others eyes: confident, intelligent, successful, independent, driven, beautiful.

(For what it’s worth, I almost deleted that last sentence because it makes me uncomfortable. Ugh.)


I believe each experience gets me closer to the right one. I learn from each date, each experience, both good and bad.

And each time I meet someone new, when the initial contacts are positive, it’s hard not to hope that maybe this could be the next one. I won’t say “the one” because I don’t believe it to be true. I’ve fallen deeply in love a couple of times in my life, and I believe I may have a few more in store.

I did a thorough professional leadership assessment this year, which included a number of clinical psychology tests and interviews. One outcome I found interesting is I am apparently exceptional at reading and understanding people. Top of the chart results – a combination of reading faces, emotions, and listening. My emotional intelligence score was one of the highest they’d seen.

So you’d think perhaps I couldn’t be fooled, but it still happens.

I’ve always been a very trusting person. I believe people are good-natured and have good intentions. I believe people tell me the truth when I ask them questions. I value transparency and expect it from others.

But that’s not how the world works.

I have a combination of tendencies which get me into trouble. First, I put myself out there over and over, because I believe it’s the right thing for me. I believe by trying something 100 times, I may have 20 shit experiences but will have 80 decent ones. Or at least not horrible ones. I tend to believe the next interaction could be a really great one.

Second, I believe what people tell me unless they give me a reason to doubt them. Yes, I can spot catfish and men who are clearly lying about their motivations. My dating rules have helped me – and I put them in place so I could have a method for overcoming my natural optimism.

Third, I desire to see the best in people. Hy calls me a diplomat, to a fault. I am so interested in people’s behavior and intentions and what makes them tick that it can blind me to what’s right in front of my eyes: their actions. My world of grey has a downside, for sure. I can come up with all kinds of reasons someone may not be in touch, when the bottom line is – if they wanted to be, they would. We all make time for the things which matter.

To make things even more complicated, it’s so easy to read what I want into other people’s words and actions. We all see the world through our own eyes, after all. I’ve written before about confirmation bias – believe a guy is a douchebag and his 24-hour silence means he’s ghosting and not into me. Believe he’s super busy with work and his children, and his actions have a different meaning.

I see it in blog comments regularly: people’s interpretations of the scenarios I describe can be very different based on your experiences. It’s completely normal.

So when I believe a man to be a “good guy”, that he wants more than just sex, that he values what I have to offer? I don’t always see the other signs. I hope for the best while trying to expect the worst, but generally, I suck at that.

It’s hard to not hope. My natural hope and exuberance got me in trouble recently. However, the moment I lose my natural inclination to get excited each time I meet someone who on the surface might be right, well, then I think the douchebags will have won.

I’m not going to let that happen.

don't let the douchebags get you down - dating disappointment

Main image is from The Wizard of Oz. The second image is from an internet search; the referenced WordPress site appears to be down. I read recently about the terrible treatment Judy Garland faced on the set of the movie, even by the Lion, Tin Man, and Scarecrow, which made this cartoon even more appropriate.

8 thoughts on “Don’t let the douchebags get you down: optimism in dating

  1. “So when I believe a man to be a “good guy”, that he wants more than just sex, that he values what I have to offer? I don’t always see the other signs.”

    I think we ALL do this, and to go further, we not only don’t see it, we *refuse* to see it: We make excuses and we justify and we reason because we WANT to believe something.

    I think that’s why *other* people’s genuinely objective views can help. I know they aren’t ever truly objective, but they aren’t clouded by being in the middle of it and having all the feels.

    It still makes me laugh that I put your own words in a presentation box and showed it to you that time: ‘SEE?! SEE??!!’ 😀

    Blogs are good for that external viewpoint :).


    • I do think that was one of my favorite things you’ve ever done. For me, I mean. Yes, I hated it at some level, but you were right (obviously!). I know I can get very twisted in my own analysis and introspection, and am very forgiving for things when I shouldn’t be… I’m better than I used to be, but it still happens. And you’re right (again, obviously), it’s one thing that’s great about blogging. People say ummmm Ann? WTF are you doing?


  2. For me you are truly all of what you wrote: confident, intelligent, successful, independent, driven, beautiful and more! I admire you and I look up to you <3 Glad you had some good fun with Lewis.

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