Dating a man with bad teeth

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

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Rejection/lack of connection is the default setting. I have limited time and energy to spend on someone I’m pretty sure I won’t click with. I’m not everyone’s cup of tea – I don’t want to be.

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. 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?

That’s why I advocate for asking people out sooner rather than later and without a sense of entitlement or getting too invested. 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. (Update as of 10/2012: Currently dating a considerate smoker who never smokes around me. ) Want to tell me about how you love Ron Paul or your favorite book is ? 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.

You are going to not going to connect with many people. I 100% defend their right NOT to date me or even spend a single second thinking about me.

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.

Mentally and socially I’m a mess, but I’d go way over 500 words if I tried to describe it all. 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.

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. 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.

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