Miss Information: I missed out on my formative dating years. How can I find the flat-brimmed weed toker of my dreams?

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Dear Miss Information,

I’m thirty-four and haven’t had a serious relationship in years. I’ve struggled with health problems and now am pretty much healthy, but I missed those major-dating years. I don’t like the pity-party thing but I also don’t know how to approach the subject with guys. Also, I’m into flat-brim guys and guys who smoke ganja ( although I don’t) and have a good laugh, tats and piercings, etc. There are none of those here in Boston and I really don’t know what to do as an alternative. I looked at online personals, but everyone has these clever, gorgeous photos. Any suggestions? — Fatalistic Femme

Dear Fatalistic Femme,

Let’s do some myth dispelling.

Myth #1: There is  such a thing as "major-dating years."
Do you know what "major-dating years" are? Any year in which you are dating. The economy is in the toilet and more people are pursuing romance than ever. In the U.S., the average age to marry is roughly twenty-seven. A first marriage that ends in divorce lasts about seven years. You’re thirty-four, which means you’re perfectly positioned to bat clean-up and you live near a major metropolitan area. If you didn’t snag someone this first go around, you’ll snag them in the second. Not saying the former has to (or should) be a goal, just giving you a little ammo to quell your runaway imagination.

Myth #2: A picture-perfect past, present, and future is a prerequisite for dating.
You’ve had health problems. So what? Other people have had kids, divorces, stalkers, bankruptcies, criminal records, and fines for cat-hoarding. Don’t worry about approaching the subject, because you shouldn’t be going anywhere near it. This is not to say your health (or lack thereof) is anything to be ashamed of. But your only responsibility in the beginning stages of courtship is to be charming, polite, and entertaining. The only exception I can think of might be the gentleman who revealed to me on a first date that the medicinal smell emanating from him was the result of a stab wound given to him by his ex-girlfriend. Nice guy or no, in that instance, it would have been better if he had taken some time before resuming dating.

Myth #3: Hats, pot, tattoos, piercings, etc. actually matter.
You’re thirty-four, not thirteen. You don’t date someone’s fashion or recreational-drug choices, you date their character. It’s cool to have a particular "type" but it’s also limiting. When you say a guy has to dress a certain way or be into certain bands, it puts up an artificial barrier. "But it means something that he likes Built to Spill!" Oh come on. It means something more if he hates Built to Spill but cheerfully buys you tickets to their next performance, then goes to the bar with you even though he has an early-morning meeting. You like what you like, but keep an open mind. There’s something hot about almost everyone. You just have to be look for it. The "good laugh" you mentioned earlier? That kind of stuff is where it’s at.

Myth #4: People look like their profile pictures.
Some people do, but they’re usually not the ones in the "clever, gorgeous photos." Those are the result of makeup, Photoshopping, and artistic license. If Boston in anything like New York City, most people are one step removed from a makeup artist and photographer, if they aren’t one themselves. Ask around and get some glamour shots or go with something more simple. The latter is better, in my opinion. Most people see right through the artificial stuff, anyway.

Dating isn’t easy. But it’s not that hard, either. The only way to get better is to practice.

Readers, any tips of re-entering the dating scene after an extended absence? What about finding handsome, flat-brimmed weed tokers in the greater Boston area?

Dear Miss Information,

I have finally been coming to terms with the fact that, although I am a high-minded gentleman of thirty years, I don’t wish to be. I wish to work in a team environment on group projects and be dominated by a woman or a group of women.

Proclamation in mind, how do I act on this? I’d rather meet a woman on the street — or on the bus — than go online looking for a partner. I don’t yet know how to say, "I want my orgasm delayed by whatever means you think are necessary until you are fully satisfied." I’ve been in one relationship where I was the sub, but her life was a mess and it was clear she just wanted a little entertainment rather than a full-blown relationship.

It took a lot of courage to even put this out here in the first place. I realize how my failure to be honest about this need has made me a bad lover in some cases. I feel like I need this discipline to iron out other issues I have. I frequently flog myself as an outlet. I’m also looking at therapy, but I haven’t had sex in months and finally knowing what I really want makes this a goal. — Sub Boyfriend in Transit

Dear Sub Boyfriend in Transit,

You have a specific fetish. One that you’re shy about expressing. Yet, for some reason, you’d rather risk getting thrown off the cross-town bus than do what all other tongue-tied and kinky people do: that is, sit your begging-to-be-spanked butt down at the keyboard and find yourself a dominant wifey. I’m sure I could find a way to water ski in my bathtub if I had a couple milk jugs and a hairdryer, but life is already hard. Why make it harder?

Online you’ll have the freedom to say exactly what you want, as privately as you want, without having to worry about flubbing your lines or losing your composure. You can weed out those looking only for a fling and conduct Google background searches to cull the number of opportunists and psychos.

Of course you’ll still meet some unsavories, but compared to the alternative — picking up a stranger and hoping that she likes you, is available, and is cool with your sexual proclivities — it’s a much more effective way to go. You’re relationship-minded, so that’s a bonus right there. There are a ton of women who would love to meet a guy in your situation.

If you insist on meeting a woman the old-fashioned way, I’d wait to disclose the extent of your preferences until you get to know each other. And I’m not talking about the second date. I’m not even talking about the first few times you have sex. (If that means the first few times you have sex are mediocre, oh well.) If you want to find something lasting, start with vanilla sex first, then gradually introduce your fantasy. If someone digs their partner enough, they’re  usually able to adapt to almost anything. If not the specific thing, then some modified version thereof. What you want to make clear to her is that you’re into her first, then the kink.

I see no harm in flogging yourself (other than, uh, you’re flogging yourself) provided it doesn’t become a compulsive behavior and you’re doing it safely. Like you said, you’re new to this and it’s a way to explore without fear of judgment or rejection. Another outlet might be seeing a professional dominatrix, although if you’re seeking something more serious your money might be better spent on the aforementioned therapy. Look for someone open-minded and accepting of alternative lifestyles. Seeing a therapist who wants to talk you out of your desires would be counter-productive.

Readers, any tips for a new sub? Do any of you flog yourselves? I’m curious about how this works. The only ways I beat myself up are mentally…