"Blow jobs can be taught much more easily than emotional stability can."
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Dear Miss Information,
I'm 23 years old and I've never been in any type of relationship. This is largely due to the fact that I suffered from serious depression from high school until my sophomore year of college. Because of this, I was very socially awkward and didn't even go on my first date until I was 21. Since then, I've dated a few people for extended periods of time, but none of them were exclusive.
I'm at the point now where I want a serious relationship and I recently started seeing a guy that I really like. However, I have no idea how to approach this subject and I fear that it's a deal breaker for most guys my age. In the past, when guys have asked about my past relationships I've quickly changed the subject. But I know that if I want something serious with this guy that I should be honest.
So my question is when and how should I bring this up in a way that won't scare him off?
—Inexperienced in Love
Letters like yours, the "I'm behind the curve and here's why" variety, always break my heart a little. Because here's the thing: everyone has their own thumb print of relationship experience. Some of us party with rock stars, lose our virginities at 16 in the back seats of classic cars, then settle down to domestic bliss at 21. Some of us spend most of our lives dealing with health or mental issues, or taking care of our ailing parents, or reading very dense books, then —Bang!— fall in love out of the blue at the age of fifty. Rather than fretting that you don't know how to give him the BJ Of His Dreams à la Cosmo, consider that you took the time you needed to become a more solid person, you emerged triumphant, and that solid footing will set you up well for your future relationships.
So, first I want you to re-frame how you think about your past. What if that long period of "awkwardness" was actually seasoning you to be a better person? Teaching you the kind of introspection and honesty that good relationships require? Making you really good at getting yourself off, which will make you better able to direct others? My point is, Inexperienced, give yourself some credit. You're off to a better start than you think. And when it comes up in conversation, talk about your dating fallow period like a strength, not a weakness. Because it is. It made you into the person you are now, the person this guy presumably cares a lot about. Blow jobs can be taught much more easily than emotional stability can (a slogan I now want to emblazon on a tote bag).
Regardless of one's relationship track record, the "I like you, do you like me? Check Y/N" conversation is always delicate. You can take the ripping-off-a-band-aid approach of, "I really enjoy seeing you, and I'd like to be exclusive. What do you think?" You can hire a skywriter or give him a binder of pictures of him sleeping with adorable captions you wrote in glitter pen.* The options are nearly endless! It may be an awkward conversation, as important conversations often are. If it's a deal-breaker, that's his loss, not yours. Keep on your trajectory and make no apologies. You're not behind; you're right on target.
*Heads-up: if you actually do this, I won't be your one phone call from jail.