Swinging with Insecurities

Thomas Ruff OBE 08_2001
Thomas Ruff ‘NUDES OBE 08’ 2001

HIM: I belong to a hilarious Facebook group called Bad Business Ideas. One of the members there recently posted this stroke of genius: “An app that lets you know six months later that that girl was totally hitting on you.” In the comments, another member suggested that the app be called Hey Dumbass. Like most humor, much of the appeal comes from striking a raw nerve. This one certainly did for me. Two stories from my past come to mind. 

When I was 21, I worked part-time at a pizza restaurant in a b-list amusement park. One evening, the manager asked me to go downstairs to retrieve a beer keg from refrigerated storage. A very pretty co-worker I had talked to a few times in passing volunteered to go with me to help. We had to search around in the dark, deserted basement for quite a while before finding it. It wasn’t until the next day that I figured out that not only was the keg small enough for one person to carry, but that she had no experience to make the task any easier. She did her part – she arranged to be alone with me in a secluded place. I, on the other hand, worked as hard as I could to find the beer keg and get it upstairs.

You’d think time and maturity might make things better, but that didn’t turn out to be the case. In my mid-thirties I had a very intelligent, very attractive assistant. She was slim, had surprisingly big, natural breasts, and a beautiful face – not to mention a very charming English accent. I was a bit of a workaholic in those days, so almost every Friday she would ask me if I was coming in on the weekend. Almost every time I did, she would also appear to “catch up on things,” even though it would be fair to say she was under-utilized from an office productivity perspective. Oh, and if the weather was warm she’d be wearing shorts and a tight t-shirt. This must have happened at least 15 times. Yet it wasn’t until two years after she left the company that I figured out what is obvious to you. Two years!

It now seems clear to me what was going on in my mind in both situations. I was super horny, and both women were outstanding relationship material: a perfect combination. Yet a force more powerful was at play. I was looking at the situations – the unnecessary offer to help, the perfectly timed appearance at the office – that led to us being conspicuously alone together, and thought the LEAST LIKELY explanation was that they were coming on to me.

HER: I think I understand. For me, it wasn’t the opposite sex I thought couldn’t like me, it was other girls. I have always felt more comfortable with men, maybe because I grew up with four brothers, or maybe because I knew I had some sexual currency that could explain why guys would be interested in spending time with me. But connecting with other women has never been easy. I always imagined, if girls invited me out or included me in their group, it was out of pity because I was such a shy bookworm. I thought everyone saw me the same way I saw myself: as a bit of a loser. I couldn’t believe they actually wanted to spend time with me. But I’m sure most of those invitations were genuine.

HIM: I know they were genuine, but it doesn’t much matter if you can’t see it. Low self-esteem comes in many varieties, and you will become well acquainted with your own unique version if you spend any time in the lifestyle. Here is the negative loop programmed deep into my subconscious: I believe I am attractive in appearance and personality, yet I firmly believe it is an attractiveness that almost no woman could ever be attracted to. Strange, I know. No one said our primitive brains have to make sense!

HER: That really doesn’t make any sense. I know your previous (nearly) sexless marriage didn’t help you feel more sexually attractive. But did marrying me change anything for you, or do you still feel like you struggle with those insecurities?

HIM: That should have settled things. All this should be ancient history now. You’re a smart, beautiful, very sexual, talented, and practical life partner. My frustrations would be a laughable story from the past, except for the sexual adventures we’ve embarked on. And you know what? It turns out that my ‘no woman could ever find me attractive’ conviction is still there, undiminished. When another couple check us out on the dance floor, I am certain that the woman is not interested in me, and that both of them are really just hoping to get it on with you.

HER: I would find that hard to believe if I hadn’t seen it in action. You come across as so positive and confident, but whenever we talk about who we find appealing at a club or party, you seem to point out the less-than-attractive women. Not that there’s anything wrong with liking people who aren’t model material, but you never choose women who are in your ‘league’ in my estimation. It always makes me a little sad to see your low expectations of yourself reflected in your choices. You’ve worked hard your whole life to stay fit, you dress impeccably, you’re incredibly smart and respectful and successful, yet you don’t seem to understand that those are exactly the things women are looking for. You could have any woman in the room!

HIM: You know what? I almost agree with you. I generally walk around thinking I could marry any woman in the room. I know that sounds arrogant yet, for some reason, that’s not what I long for. I get that I’m good husband material, but I guess I want to be good fantasy material. The problem with primal certainties is that they are not very susceptible to reason (have you talked to a Trump Republican lately?).

HER: I know. It’s easy to say confidence is sexy, so just believe in your appeal.  But it’s hard to rationalize your way through a deeply-held belief. I still feel like that loser from high school sometimes even though my ugly-duckling phase ended in eleventh grade. I get it.

One of the fun things about the journey we’re on is that we get to date lots of people with little risk. I think we’re both in the best place we’ve ever been as far as attractiveness. On top of that, we’ve already secured our life partner, so we have nothing to lose: no matter how the night goes, we never go home alone. It’s like being able to fulfill that fantasy so many of us have of returning to high school with the confidence we earned post-high school.

By the way, you should know that the thing that made you stand out to me initially wasn’t your marriage potential. It was your ass, pure and simple.  That and your great conversation skills. But mainly your ass.

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