Dear Dana: Are My Looks To Blame For My Dating Disasters?

Dear Dana is a bi-weekly advice column for humans who engage in romantic relationships. Please send your dilemmas, issues, conundrums, assumptions, conflicts, anxieties, worriments, obstacles, complications, predicaments, queries, questions, and any other synonyms for “problems” to

Dear Dana:

I’m 35 and single. I’ve been trying my hand at online dating for the last year and haven’t gone on a single second date. There have been plenty of guys I’d love to continue seeing, but after our first date, I never hear from them again. I’m beginning to think it’s my looks that are holding me back. I’m smart, well educated, well traveled, and have an interesting career, but I’m not much to look at. Honestly, it’s the truth, and for the most part I’m OK with it. I have plenty of other gifts. The problem is I really want to be in a relationship, and no one seems willing to get past my exterior to get to all the good stuff.

So my question to you is: Should I try to improve my appearance in order to catch a guy? Should I lose some weight? Overhaul my closet? Try some new makeup? Maybe even invest in a push-up bra? Would these things help me at least get a foot in the door?


Ugly Betty


Dear Ugly Betty,

When I was online dating, I kept a spreadsheet. Here are my stats:

Screen Shot 2015-01-29 at 7.36.29 AM

It took me two years of semi-constantly browsing of profiles, writing messages, going to coffee shops, and awkwardly adjusting my skirt when I hoped he wasn’t looking to acquire those numbers.

I pretty much wanted to date everyone. Did you go out with me once? Odds were good that, regardless of who you were, I was charmed and wanted to give our love a shot. I was desperate for another evening of shared mozzarella sticks and a list of all the clubs you were a member of during high school. I wanted to really get to know you, random dude who wasn’t especially interested in me. I wanted to make you my man.

I wanted to be liked, and then loved, and then told that I could delete my online dating profile forever. I wanted a relationship and I wanted one so badly that I was willing to go out again with the dude who farted eight times before our drinks arrived and told me that his favorite movie was “Love Actually.” I thank science that most of the dudes I was willing to date again decided not to date me because someone has to have the good sense to end a terrible relationship before it gets started.

The vast majority of the people who you date will not want to date you again. This statement is unique to neither me nor you. This statement is the one true fact of online dating for all humans. This is a true fact for anyone at any time at any level of attractiveness. It is true because an online date is not an actual date—it’s an interview to see if you’re going to get to go on a date. And most of the time the answer is, for reasons you will never know, “no.”

But sure, you can totally change your outward appearance with the goal of going on a second date with a stranger. You can buy new clothes that you aren’t sure that you like and you can do that new/old/terrifying contouring makeup thing on your face. You can wear shoes that pinch your feet and a push-up bra that digs into the soft flesh below your armpit. You can start doing P90X and eating nothing but broccoli and greek yogurt. You can look at dating as a marketplace and yourself as a commodity and you can work to turn yourself into a commodity that will attract a larger pool of dates. But why the hell do you want to date someone who wants to date a person who does all of that nonsense?

I don’t know what you look like. But the line, “I’m not much to look at,” made me want to flip a table.

You may think that writing this line means that you’re being bracingly honest. I think it means that you’re full of shit.

There have been a few people in my life who have referred to themselves as “not much to look at,” and they have all been devastatingly wrong.

You don’t know what you look like. None of us do. We are all the worst judges of our own appearance. And your assumption that you’re not much to look at and therefore your potential mate will simply have to settle for a woman with a great education, career, and passport is insulting. To them.

It is your contention that you are physically unattractive that has made you unattractive. No one wants to date someone who doesn’t like themselves. No one wants to date someone who is ashamed of the way they look.

Do not do yourself the disservice of presuming that it is your looks that are preventing these men from dating you. It is far more likely your dismal view of yourself that’s signaling them to stay away.

You need to give your date the courtesy of not assuming that he’s repulsed. You need to know that attraction has little to do with how well you conform to the ideal cover model image of beauty, and everything to do with the chemical combination of you and your partner. You need to see the beauty that you already have. Ask your friends. Look at yourself and work to see what is actually there, without the lens of negativity or self-doubt. If you weren’t you, what would you think? If changing your hair or buying a new dress will help you to feel better about yourself, go for it. But know that I am convinced that you are already wonderful to behold.

As for getting your foot in the door of second date, what’s going to help is saying, “Hey, this is fun. I’d like to go out with you again.” The act of asking for the thing that you want contains an astounding power.

But don’t run around throwing that line at everyone. Make sure that he’s really worth another one of your evenings. Make sure he’s more interesting than your favorite TV show or your friends or your book.

Stop wondering how you can change your appearance to make yourself more worthy of these men’s time—start making sure that they’re worth yours.

Dana Norris once went on 71 internet dates, many of which you may read about here. She is the founder of Story Club and editor-in-chief of Story Club Magazine. She has been featured in McSweeney’s, Role Reboot, The Rumpus, and Tampa Review and she teaches at StoryStudio Chicago. You may find her on Twitter at @dananorris. 

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