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Question #162: Bad teeth and other dating dealbreakers.

Chris Traeger from Parks and Rec

“I have endeavored to become perfect in every way. Ann Perkins!”

Happy New Year, Awkwardtown! I apologize to RSS readers- this post prematurely went up before I was done with it. I’ll be letting comments through again shortly.

This week marks the 1 year anniversary of this blog (January 4th!), and to, uh, celebrate this milestone I will be posting a ton and gently directing readers toward the Donation Page all week as part of a twice-yearly pledge drive (in lieu of running ads). If you enjoy yourself here and can spare a few $, I appreciate them and put them to good use.

If you can’t contribute financially, I completely understand and hope it doesn’t make things weird between us. The readers and commenters contribute so much to the community here. I didn’t know back when I started this thing that I was, you know, starting A Thing, with Jedi Hugs and FEELINGSBOMBS and African Violets. Thanks to you we have one of the best commentspaces on the Internet, and letter writers can always depend on you to support them and help them out.

On to today’s question, which is about how you seek a romantic relationship when you are insecure about some aspects of yourself.

Dear Captain Awkward,

I really enjoy your blog and the comments. I found my way here after reading this series on depression:  That made me realize how depressed I’ve been, and around my birthday a few months ago I decided to do something about it. Part of my problem is I haven’t been in a relationship in many years. So I signed up for some online dating, but it’s been tough. Once I found your blog I took a couple weeks to read through your old questions, some of them were very relevant to my issues.

http://captainawkward.com/2011/08/22/guest-post-how-do-i-stop-letting-my-terrible-self-esteem-sabotage-my-relationships-reader-question-99/ (comment: “Sure, they notice if you are sloppy, or not practicing basic hygiene and grooming…”)
http://captainawkward.com/2011/06/28/reader-question-67-my-wonderful-boyfriend-has-horrible-hygiene-and-a-disgusting-house-how-do-i-talk-to-him-about-it/ (one comment stuck out: “Poor dental hygiene to me is a total, permanent deal-breaker.”)

About me: I’m a hetero male, nearing 40 years old. Mentally and socially I’m a mess, but I’d go way over 500 words if I tried to describe it all. Physically I’m about 80% happy with myself. I’m tall, not overweight, somewhat fit but not too obsessed about it, full head of hair (graying but that’s OK), and…horrible teeth. It’s embarrassing to talk about, but these last few months of trying online dating have kind of broken through my shyness. Years of neglect while playing video games and being lazy have screwed me up.

I hate myself for letting it get like this, because now I feel as if I’m not able to get a date. Most women want a confident man that is a good kisser, and I am neither of those. Bad breath, missing teeth, discolored smile, and never had many girlfriends when I was young, so don’t have much kissing skill. I am rather self-conscious about it, but I don’t have insurance and can’t afford to get any work done right now. Meeting women is hard because when (if) they flash a big smile (with their nice teeth) at me I just can’t do a big, natural smile back at them. I just *know* they’ll notice how bad things are and be turned off. It looks bad in pictures, too.

Reading through question 99 again…so maybe looks don’t matter and it’s mostly in my head. What about kissing, is that not important in an intimate relationship? Is this a deal-breaker to most people, or is it mostly just my lack of self-confidence that’s an issue?

Thanks,
Embarrassed to Smile

Dear Embarrassed:

I did say all that stuff, so, sorry: Your teeth might be a dealbreaker for me in feeling attracted to you. But in faux-comforting news, the dealbreaker might be something else entirely!

My fat body is a dealbreaker for many people. They will not be attracted to me because how I look. No matter how cool dorky cool I am, no matter how much fun they might have talking to me, no matter how much I might check off every single item on their dream girl checklist, it’s a nonstarter. Or it might be something else, like how I always think of the worst possible thing to say for any occasion and many times my filter does not catch these things before I say them out loud.

We talk a lot about “Rules of Dating” here, but let me throw some big ideas out there about attraction, fairness, and what people “deserve” in dating:

1. Everyone has issues.

Everyone has something about themselves that might be a dealbreaker for someone else in becoming attracted to them. Everyone is self-conscious about something. To be human is to be imperfect. I don’t believe that you must smooth all your imperfections (or what society perceives as imperfections) away to become a thin, (straight, white), wealthy, positive! blindingly-teethed Chris Traeger-bot before you deserve to put yourself out there, meet people, and try to find love.  The truth is, even if your teeth were great and your life were somehow perfect, you’d still have issues about something, and if you didn’t personally feel that you did, the culture would try to make you have them. Anyone who tells you differently is selling something. “No one will love you if you don’t fix yourself” is a *great* way to sell things. It is *the* way to get us to lie down in Procrustes’s magic bed of our own free will.

2. You get to reject people (and they get to reject you) as dating partners for any reason at any time.

You don’t have to be fair. You don’t have to give anyone a chance. If you’re talking yourself into feeling it for someone, that’s a sign that you are NOT actually feeling it.  Which also means people get to make snap judgments about you and decide, “Nope,” and there is no way you can “deserve” attention or affection from a specific person. That’s why I advocate for asking people out sooner rather than later and without a sense of entitlement or getting too invested. You are going to not going to connect with many people. Rejection/lack of connection is the default setting. It feels different to be passed over by a stranger than it is to be turned down by someone you’ve been pining for after you’ve made a grand gesture. You’re giving the person in the second (overly-invested) scenario WAY too much power over your happiness and forgetting that they get to make a snap judgment.

I used to go on a lot of dates with strangers. That’s how I ended up here. Now that I’m older, I embrace the pickiness. I have limited time and energy to spend on someone I’m pretty sure I won’t click with. For example:

I once met a guy who had seven cats. “That’s too many cats,” I thought. No second date.

Smokers? I’m asthmatic, and even the residue/smell on clothes triggers my wheezing. We are works in progress, so maybe a year from now you’ll be an ex-smoker and I totally missed my shot with a great guy. Whatevs! (Update as of 10/2012: Currently dating a considerate smoker who never smokes around me. Never say never!)

Want to tell me about how you love Ron Paul or your favorite book is Atlas Shrugged? Sorry, my vagina just sewed itself shut. You shall not pass.

Your profile lists 10,000 supercool books, bands, and movies  and all of it was made by white men? Bored now.

You live in a place not reachable by public transit? How can we date, since I am never going there?

But 1,000s of guys are looking at my profile and thinking, “fat AND broke AND kinda sarcastic and mean? No way, Jose.”  Some of those take time out of their busy lives of  “watching the Cubbies with my bros!” and “just trying to living life to the fullest”  to call me names and remind me that I shouldn’t get to be picky or “judgmental” about men when I am such a fatty-fat-fatty (manatee, cow, pig, whale, she-beast, etc.)  They feel “tricked” into “wasting time” looking at my profile.

What they don’t understand…I mean, one of the many, many, MANY things they don’t understand…is that I think that they get to be picky, and that I also get to be picky. I 100% defend their right NOT to date me or even spend a single second thinking about me.  I’m not everyone’s cup of tea – I don’t want to be. For a handful of people I will be just what they want, and they will be just what I want, and who cares about the rest?

What we should also understand, in the name of complete honesty:  If you scrape the surface, many dealbreakers stink of sexism, size-ism, classism, able-ism, and racism. As a straight white woman, I get more messages from suitors than others might. I personally privilege men who have a strong command of language, spelling, and grammar, which means I may be passing on some great people who suffer from dyslexia or who didn’t have the same educational opportunities I did. The guys who call me names are under the sexist impression that women are supposed to be ornamental in a certain way, and if we’re not we are completely worthless. Someone who rejects your bad teeth is rejecting your history of depression and the resulting poverty or lack of self-care. This is problematic, but on the micro-level, what are you going to say to someone who rejects you for an “unfair” reason?  You can’t argue someone into liking you when they don’t. In fact, someone who tries to argue me into liking him has inadvertently discovered one of my dealbreakers.

So let’s talk about that lack of confidence. Everyone talks about having confidence in dating. “You gotta have confidence. People like confidence.

It feels like a trap. I mean, how do you get or fake confidence about the very stuff you’re not confident about? Maybe think of it as less about having or faking confidence and more about not projecting your insecurities all over other people in an icky way. Like, maybe you have tons of uncomfortable emotions about your teeth, but you know how to take care of yourself around them and not make them other people’s problem (especially when you are meeting and early-stages-of-dating new people). The way I see it, people might find my fat body unattractive, but they will find me unattractive if I make it a giant issue of it and blame it for everything that is wrong. “You probably won’t like me!” “I bet you’ll reject me!” “I will try to be extra self-effacing so I become worthy of your attention!”  is not a good cologne.

So when I take this fat ass out on a date, I drive it like I fucking stole it. I make zero apologies for it. The world is full of people who will tell me I have the wrong kind of body and tell me I should hate myself for it, why should I help them with their work?  I relax, I tell myself “Self, you can have a conversation with anyone for one hour and make anyone feel cool and paid-attention-to.” I try to get to know the other person, I try to figure out whether I even like him, I check in with myself to ask “Self, are you having a good time on this date?”  I ask “Can this person keep up with us? Is he as cool as Commander Logic?”  I save the problem of how much or whether he likes me for later. It’s not my problem, because it’s totally out of my hands. If he likes me That Way and I like him That Way, too? Dumb, awesome luck, and the exception rather than the rule. If I sat there the whole night worried about my fatness? The guy would not like me at least partly because I would be a bad date for wallowing in my insecurities instead of connecting with him.

So you’ve done some hard work at pulling yourself out of depression and getting your life together, and you’re ready to meet people. While I do want you to take care of your teeth to the extent that you can now (floss, brush, use a tongue-scraper, mints, mouthwash) and seek professional care as soon as you can,  I  vote that you take those mossy Shane McGowan teeth of yours out on the town. Take a page from his book (the one that is inscribed “I do not give a fuck. Love, Shane McGowan”) and meet some ladies.  Some ladies may not want to kiss you, but you can’t really know which ones in advance or control it. You might as well try smiling when you feel like smiling and generally not giving a fuck.

Happy New Year! Give less of a fuck!

Thanks in advance for any kind support you can offer.

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About JenniferP

Chicago filmmaker, teacher, and blogger.

40 comments on “Question #162: Bad teeth and other dating dealbreakers.

  1. This is an awesome answer.

    I just want to add that the confidence thing was confusing for me as well. I try to think about it as letting my personality shine out. Despite your physical anxieties, there is a personality inside you that someone out there finds compelling. Now that I have found my guy, I know that I didn’t have to do anything but be me to land him.

    I like this quote that wikipedia attributes to Jodi Picoult “You don’t love someone because they’re perfect. You love them in spite of the fact that they’re not”.

    Good luck to you LW.

  2. If you live anywhere a university dental school, you can get practically everything done at a very modest price. The work is done by about-to-graduate dentists under the CLOSE supervision of their professors. I had quite a bit of work done at the NYU dental school years ago.

    Getting to work on your teeth is very important for your health. Low-grade infections in your mouth cause lots of problems in the rest of your body in addition to making you feel terrible all the time. It’s not just an aesthetic thing. And decayed teeth are so uncomfortable and smell bad.
    Take care of yourself.

    • For your dental-school/teeth-fixing/self-esteem-growing inspiration: http://smilepaul2011.blogspot.com/

      The Captain is totally right, as usual, on the dating front. But also, if you can find a dental school that works out a plan with you, you can go from mouth o’ broken dreams to nice smile with a less outrageous amount of money (but an actually outrageous amount of patience with yourself).

  3. I drive it like I fucking stole it.

    Awesome metaphor!

  4. Unfortunately, here in the U.S. having good teeth is a class marker, like having a reliable car (if you don’t live in a big city) or owning a house. In the near future I am facing either tons of really expensive dental work or possibly not being employable if I should lose my current job. It’s not fair nor is it particularly rational, but there it is.

    That said, the good Cap’n is totally on the ball when she says to just smile anyway. You go to dinner with the teeth that you have, not the teeth you might want or wish to have at a later time. And you can’t hide them without your date wondering OMG what is wrong with this person? The wondering is way worse than the knowing.

  5. Re: kissing — I will go on record as saying kissing is SUPER important to me, BUT. My best kiss with someone has never been my first kiss with someone. Like pretty much anything else in dating, in my opinion/experience, while there are certain good rules of thumb (don’t just like… unhinge your jaw and keep it there while you poke your tongue around; easy on the tongue especially at first) kissing is less about Doing It Right and more about figuring out what works with you and the person you are kissing with. The best advice, I think, is be responsive to what they’re doing, and the two of you will work it out. Sometimes it takes a while for two people to find their rhythm, and maybe that would be a dealbreaker in a one-night-stand scenario, but it doesn’t seem like that’s what you’re after. My hunch if that if someone feels enough of a spark that a date could eventually turn into Dating they’ll be willing to put up with a bit of a learning curve.

    Also, you might to read this Dear Sugar column, as it addresses a dude in similar straits http://therumpus.net/2011/01/dear-sugar-the-rumpus-advice-column-63-the-magic-of-wanting-to-be/

    Good luck to you in your endeavors!

    • I love that Dear Sugar column to pieces, thanks for linking.

    • That’s a top 5 advice column post for me! You’re not unlovable, LW. I went on a couple of dates with a guy, and I was feeling it more than he was. In the end, he said, “You’re awesome, but I just don’t think we’re going to work romantically.” I was upset, yeah, because I saw something more, but if someone says this to you, it’s not about your teeth. Trust me. It’s about them, and that’s all there is. You will date other people. They will like you if you’re taking names and not trying to hump everything that moves. Love yourself, take care of yourself, and people will notice you have a passion for life. And passion? It’s awesome.

  6. I went through this a few years back. I had crippling shame because I was with someone who treated me as though I had all these “bad things” — I was too fat, too old, too smart. And in retrospect, I cannot BELIEVE I fell for that shit. Because I went out on the scene and found out that I’m just perfect for a lot of people! And my ex was just an asshole who exerts power over people by whittling away at their self-esteem.

    No matter who you are, whatever your failings, they are *not* as big a deal as you think they are. There are so many options that do not conform to this fake pop culture ideal of “good.” And you will find them, they will find you, and the best result will be that person around whom you can just CHILL and relax and be happy.

    Go get em!

    • Also, to the LW, I find that the older people get, the less hung-up they are on mainstream “good.” Women over 30 tend to be more open about what they like and they will tell you if they want A or B, whereas 18-year-olds frequently have no idea how to say that out loud. You’re forty, so there is a good chance you’ll be able to talk straight to someone and they won’t blow you off because you aren’t a movie star version of next-door joe. Pop culture doesn’t often express this, but honestly: things get better with age.

  7. Hi LW – I just want to comment to you as a woman with pretty crooked and messed up teeth. I had braces & retainers for 10 years as a kid, and they’re still crooked as hell. As an adult, I’ve had depression and lack of dental insurance problems so there’s other problems too. But you know what? My dad had crooked and messed up teeth (and he refused braces since he played hockey & was afraid a puck to braced teeth would knock ‘em all out). Crooked and messed up teeth run in my family, and I’m just as proud of them as I am of the charm (if I say so myself ;) ) and blue eyes that I inherited from my dad.

    But no one’s ever commented on my teeth being fucked, and even if they did, screw them. They’re part of me and no matter how ashamed I am of other bits of my life, I won’t be of my teeth. So – please, don’t be afraid to smile when you feel like it. When your face lights up and your personality shines through, the last thing that someone who’s into you will notice is your teeth.

    Best wishes to you, LW. Get the work done that you need and don’t be ashamed of where your life has taken you (even if it’s to places you wish you hadn’t had to go).

  8. So, I’m dating a guy with awful teeth. Missing teeth, broken off teeth — as bad as yours, LW, and worse, I’m sure. Things that are bad about that (from my perspective) are: listening to him complain about tooth pain but never go to the dentist, and worrying about stuff like heart health and other health matters that tooth decay might affect. Things that are not bad about that: everything else. I really love everything about him, and I wish he would prioritize his own health and comfort, but I’m also sick of nagging him about prioritizing his health and comfort, and I definitely never look at him and wish that I were dating a man with whiter, straighter, or more teeth, so. We are where we are.

    Anyway, I think the Cap’n already covered this, but I wanted to add that from my very own personal experience imperfect teeth are hardly a dealbreaker for all women (although I hope that the LW can prioritize his dental health and comfort for health and comfort reasons).

    The kissing thing, though. That is important in dating, I think, although I suspect the LW would be better off approaching it as a skill to be mastered and not something that takes him out of the dating scene entirely. He says that he doesn’t have much kissing skill. Would it be weird to just tell dates that, I wonder? Or rather, is there a not-weird way to put it — “I really want to kiss you, but it’s been a while since my last first kiss” — something like that? Otherwise, I’d err on the side of gentle, little tongue, let her take the lead, and make sure to brush your teeth or pop in a breath mint just before if you’re feeling self-conscious. Good luck!

    • Seconding the advice on kissing. By the time I was in college I had kissed all of… no one. When the time came to get my first kiss in I just took cues from the guy I was kissing. It didn’t go horribly, yay!

      And really, I’ve found that’s one of the best tactics to take with any physical affection when you are unsure. See what the other person seems to enjoy and try to go with the flow. Kissing is a learned skill and something you have to relearn a little with each new person. So enjoy the learning curve!

  9. Thanks for the answer, and everyone for the comments. Happy new year and blog anniversary! I’m not much for resolutions, but I’m going to try hard to make this a good year.

    1. Everyone has issues.

    True, but some are more of a dealbreaker than others. Some people like ‘fat’, but I doubt anyone is actively looking for someone with bad teeth. Ahhh it’s hard to stop the negative thoughts and excuses.

    2. You get to reject people (and they get to reject you) as dating partners for any reason at any time.

    This gets into my emotional and social issues. I’ve always been shy, even before my teeth were bad. Never asked girls out or went to school dances. Only got a girlfriend if they asked me out. As an adult I’ve been kind of isolated for various reasons. I wasted a few years staying home playing video games, never trying to meet people or make new friends.

    Now I’m not nearly as shy, but still not confident. I’m working on it, though, with a little help! Now that I think about it I’m surprised at myself for writing in to an advice column!

    I do try and take care of myself now, brushing at least daily, even flossing sometimes! I’ll look into dental schools.

    Lesley: Hey, I’m not 40 yet, give me a couple years! Still, I’m not sure about things getting better. It feels like I’m a failure as an adult on multiple levels. No good career (can’t provide for a family) and no relationship for 10+ years, and the longer it goes the worse it looks. I must be damaged goods or else I’d be with someone, right? Ahhh bad thoughts!

    OK some good thoughts…at least I’m tall, don’t have to worry about that like short guys do. I’ll try and go out on some dates instead of rejecting myself before I’ve even had the chance to meet someone. I’ll try and accept all the rejections that are sure to happen and not let them crush me. Get up and try again.

    Thanks,
    (Not Quite So) Embarrassed to Smile

    • Real quick on your response!

      “True, but some are more of a dealbreaker than others. Some people like ‘fat’, but I doubt anyone is actively looking for someone with bad teeth.”

      I would say “Some things are more of a dealbreaker for some people than others.” I regaled the Captain – and somewhere on Sexy Typewriter – recently with a story of a date I once went on that I called The Date of the Four Non-Dealbreakers. The date in question was a great conversationalist, had interesting ideas, good looking, snappy dresser, etc. If he was all of that and had ONE of the following traits, it would have been on like Donkey Kong:
      - Halitosis. This is curable with assiduous tongue scraping.
      - Misleading photo by about 40lbs. Eh. Not awesome, but not heinous.
      - Squeaky high-pitched voice. Could have gotten used to it.
      - Did not even offer to pay for any part of my dinner/coffee. I’m always prepared to pay at the very least my half, but a little Check Dance is part of the game, yo.

      Like I said, having ONE of those traits wasn’t going to turn me off. All of them together equaled No 2nd Date. But in telling this story several times, people have all kinds of different reactions. “Halitosis? I’d run for the door!” “FailPhoto? I’M OUT.” “Didn’t pay for the first date? CHIVALRY IS DEAD.”

      But the point of that story is actually that people have all kinds of dealbreakers that mean more to them than others. On a scale from one to Shane McGowan, HusbandLogic has some pretty damn British teeth. I still love him and kiss him.

      You are who you are. They are who they are. Maybe you wouldn’t go out actively seeking someone who has a chronic medical condition, or has kids, or is military, but all else being awesome, is any of that a dealbreaker? I would hope not. True dealbreakers, for me, were married guys, cruelty, and dishonesty.

      What’s a real dealbreaker for you?

      And GOOD LUCK! You’re going to have fun!

    • It may be true that nobody will actively /like/ bad teeth, but judging by comments, there are people who simply don’t care about them, and will see past that to notice other things about you that they like.

      • My super cute and indie friend shirls actively seeks out people with crooked teeth because she says people with crooked teeth always have a more interesting life story to tell than the millions of identical pearl teeth.

        And there you have it: there is always someone into something.

        • I’m probably coming here with a different definition of “bad teeth” to a lot of you guys. I’m British, a few of mine are a touch crooked, this is, y’know, normal and not in any way “bad”. Yay cultural differences or something, I suppose.

          • Crooked teeth aren’t a problem for anyone, really. Or even discolored teeth. Who would care? I certainly wouldn’t. It’s like hair length. As long as it’s clean, fine by me..

            Rotten & smelly teeth are another matter. Those you need to deal with for health reasons if nothing else.

    • Hey LW! I’m encouraged that you are an occasional flosser. That is a good start, and will impress the dental students you eventually find!

      It sounds to me like you might benefit from therapy–not because of your dating or your teeth, but because you say “It feels like I’m a failure as an adult on multiple levels.” If that’s how you’re presenting yourself to new people, well, they are not going to be as enchanted with you as if you think of yourself as hot stuff. But more important than the dating scenario is that you shouldn’t have to feel like this. You might be able to find a place in your community that offers therapy on a sliding scale payment. My friend describes therapy as having a coach for your psyche–it sounds like you could use that right now.

      • Yeah I’m sure I could use therapy. I’ve never been to a therapist. I didn’t want to complicate things too much, though, and was trying to keep the question short.

        Of course the physical and mental issues are intertwined. The details and causes of my depression and self-esteem issues are more than I want to get into right now, though.

        The comments, stories and links have helped. Feeling good for now!

  10. I kinda feel it’s a little presumptuous to be talking from my position to someone who’s been around a lot longer, but here goes anyway.

    “This gets into my emotional and social issues. I’ve always been shy, even before my teeth were bad. Never asked girls out or went to school dances. Only got a girlfriend if they asked me out.”

    That describes me, except that I sometimes did ask girls out after a month or two of getting increasingly stressed about it, and inevitably failed, in part I’m sure due to the obvious extreme nervousness. Then some stuff happened and I stopped getting worked up about it, and every so often, something happens and it turns into a relationship. This is entirely down to something that probably looks like confidence, but is actually not giving a fuck and just being friendly. It’s still a difficult thing to persuade yourself into, but a little more attainable than “Be confident!”

    Sounds like you’re thinking along similar lines with “Get up and try again.” If rejection is just a thing that might happen, a less than perfect outcome but not a disaster, and you don’t go into things fearing it, things may go better than you’re expecting.

  11. LW, it sucks that your teeth make you not want to smile – that is the worst, saddest thing (and after a bike accident a few years ago I had a similar situation so I completely empathise). smile anyway, some people won’t notice and some won’t care.

    Also, anecdata: my ex (five years together) was in his early forties (I’m in my mid 20s) and his teeth were really bad, like broken, and some decayed so he lost them. I did not care what his teeth looked like. I barely noticed. The right person will not care.

  12. [...] I straight-up love you, Captain Awkward. Share this:ShareEmailTwitterFacebookDiggRedditStumbleUponLike this:LikeBe the first to like this post. [...]

  13. I could go on a date someone with bad teeth, or fat, or say, ear hair. Less than “desirable” physical traits are what they are.

    I do have trouble going on a date with the teeth or the fat or the ear hair, rather than someone with those physicalities, and sometimes that’s how it feels when someone is really insecure about some aspect of themselves — it’s like being on a date with The Teeth instead of a person with teeth. Learn not to project your insecurities forward, and be the parts of yourself that you do like first, and you can be an interesting date. Everyone’s got something they don’t want to put forward with their best foot. Figure out what you do like and go with that.

    And no, for the record, being single does not mean you are a failure at anything, no matter how much those damn diamond commercials want you to believe that. While it’s true that you can’t find a partner while hiding inside, you’re ready to meet people now. So go for it! No one is asking you to support a family at this point in time, just to be ready to meet people, talk to them, and see what happens. Go for it. Figure out how to have fun with it. And take a break when you need one. Good luck.

  14. LW, I can’t speak to your specific mouth, but I often am actually attracted to ‘bad teeth.’ The color of teeth could not matter less to me, and I find crooked teeth really sexy. So not only are there women who won’t care, there are women like me who may think it’s cute. Just keep some mints or gum handy, and you’ll be fine.

    Also, I doubt you’re as bad a kisser as you think you are, but for the record, I would definitely not consider bad kissing skills a dealbreaker at all. Just don’t open your mouth too wide or use too much tongue, it’s something you pick up pretty fast with practice.

  15. hey LW. i’m a man with issues and low self esteem and poor dental hygiene as well. i spent years – years! my entire 20′s! – not smiling in photographs. also, ducking and avoiding photographs. because i was so embarassed about my teeth. i have a reputation for being serious, and probably some people think of me as dull too, because i smile rarely and laugh in a controlled manner. you know, though, that what people say is true that if you smile and laugh you feel better. happier, more confident, sexier, competent, etc. it’s true.

    the insecurity and low self-esteem are the things. physical imperfections like discoloured or crooked or broken teeth can be fixed, and are little things besides. as people keep saying, it’s not a deal-breaker for everybody. mostly, it’s a deal-breaker for YOU. you rejecting yourself before you even go on a date means it’s far more likely she’ll reject you. (or he, i guess)

    if you don’t go for therapy, my suggestions would be this: find time to laugh more. find things that make you smile out of pure unadulterated joy. celebrate them. start by yourself in private. slowly start adding people who you love and who love you back and to whom you aren’t attracted at all and trust and have a good evening smiling and laughing with them. eventually, start expanding this circle to include some people who maybe you don’t quite know all that well yet, or maybe are kind of a little horny about and maybe have a chance of making out with them in a quiet moment someone secluded. or not! don’t put pressure on yourself. that just makes all those anxieties about your teeth just come flooding back.

    here’s something else. love is a wonderful thing and will make you do crazy things. i don’t grow facial hair very well (thanks, japanese genes, thanks), so even while working for an Assistant Deputy Minister in the govt i would only shave once or twice a week. i fell in love this summer and she only had to gripe once about razor burn and now i make a concerted effort to shave before i see her. fall in love with someone, and you will do a lot to be your best for that person (which includes all the fun little body things like shaving, flossing, plucking monobrows, depilliating, exercising, smelling nice, having smooth skin, etc.).

    lastly, some lucky woman is going to drool a little when she finally gets you alone, finally gets you to open up and talk, and realizes she gets to practically deflower you it’s been so long since you’ve had a first kiss. start slow, pay attention to her breathing and body language, and go get ‘em tiger!

  16. When I first met my husband-to-be, he had some pretty heinous dental issues. Like you, he drank lots and lots of sugary soda while playing video games when he was growing up, and was never taught the importance of dental hygiene. After 8 years of marriage, I still have to convince him that a trip to the dentist truly is in his best interest.

    When we met, he had several rotten spots on his front teeth. His teeth were yellowed from so many years of drinking coffee, and his breath was nothing to write home about. Normally, I would say that is one of few 100% deal breakers for me. But the funny thing is, I didn’t even notice. In fact, I never truly realized how bad his dental issues were until a “friend” (no longer a friend, for other reasons) made a comment that she couldn’t be with someone with such serious dental issues. I remember thinking “wow, I guess his teeth are pretty bad. Eh, all well.”

    Maybe I’ve been watching too much How I Met Your Mother, but seriously, when you meet the right person, she will fall for you despite all of your flaws. But you can’t meet that person if you don’t put yourself out there and try, try again.

    Have faith in yourself, and smile!! Good luck to you!

  17. I actually like imperfect teeth, and I know a lot of other people who do. We’ve talked about it, because it seems almost subversive in America not to prefer perfectly straight teeth that are so blindingly white they’re almost clear.

    As with everyone, I have things I like and things I don’t– for me, wolfish incisors or a tiny hint of a snaggletooth can be really hot. But I suspect there’s an audience for everything.

    So, some anecdotal evidence to back up your slow-blooming confidence, LW. Good luck!

  18. With respect to kissing, I am finding as I gain more experience that there is no such thing as kissing “well” — it’s more about whether your preferred kissing style matches your partner’s preferred kissing style and whether you can find a common ground. Some people like more tongue, some people like less tongue. I would advise that you err on the side of less tongue because “holy crap your whole tongue is in my mouth please stop” is a way less pleasant experience than “hm, not quite enough tongue” in my personal opinion.

    With respect to confidence, Hanne Blank wrote something amazing about it in the new edition of Big Big Love which I will now paraphrase badly: confidence is not just about being confident that you are a likeable person, it’s also about being confident that if this particular person doesn’t like you, you will be okay. I’ll look up her actual words if I remember to when I get home tonight because I have a feeling that my attempt to paraphrase may not have conveyed the MAGIC I felt when I read it for the first time.

  19. [...] definitely leaving that thing where my vagina sews itself shut defensively around Ron Paul voters from the other day. That’s just the [...]

  20. LW here again.

    Long story short, I kissed a woman, and it was good. Thanks everyone for the help.

  21. In other news, straight white teeth is a pretty new requirement for us regular people, like, last decade or so news. Do you know who had terrible teeth? Robert McNamara (http://en.wikipedia.org/wiki/Robert_McNamara). Just sayin’.

  22. [...] I’ve realized is half the trick to being sexy. In the brilliant words of Captain Awkward, “I drive it like I fucking stole it.”)  It was strange and a little bit awesome that this beautiful girl got her beautiful back up over [...]

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