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Should I Date Someone I’m Not Attracted To?

Dear Yana,

I met a girl on a dating app. It was sort of an accidental swipe, but we started chatting and met up. She was really cool to hang out with, but physically, I didn’t find her very attractive. We kept talking and started spending time together.

Now it has been a couple of months, and I’m having some reservations. Even though we really enjoy spending time together, I’m just not attracted to her physically, and it is starting to take a toll. She’s getting more attached, but this is becoming more of a mental block for me. I feel like Shallow Hal, and if it wasn’t for the lack of physical attraction, things would be great.

How do I get over this? Am I just being shallow?

— Getting Too Deep in the Shallow End

Dear Too Deep,

For most people, attraction is an instant, uncontrollable urge that tends to be physically motivated. Emotional attachment and intimacy, however, is usually a slower burn. If your initial attraction sticks as you get to the know the person, it can fan those emotional attachment flames, or perhaps your automatic attraction will fizzle and fade over time.

Or maybe you’re like so many of us in the Happy Valley, and you sleep with a lot of your friends, as friendship ripens to sexual attraction — the kind of attraction that creeps up ivy-style between you and your bros when you least expect it (even though, let’s be real, everyone else around you totally expected it).

Let me get to the point: It’s okay not to be attracted to someone. And it’s okay to feel attracted to a person initially and have that desire grow or fade over time.

But there is something inside of you that’s not sitting right, Too Deep, a little piece of you that feels like maybe you’re being an asshole. I’m guessing that this woman you speak of does not nestle neatly into the box labeled “beautiful” by conventional standards?

Are you an asshole if you dump this girl? I’m not sure if that’s for me to decide. But I can tell you how I make sure that I’m not being an asshole…continue reading…

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Seeking DTF on the WWW

I’m seeking out dating websites that have individuals who are thoughtful and open to trying or having more casual sex, but also respect boundaries in sexual exploration. I don’t trust Craigslist, and I’m not really into OKCupid or Tinder.

I would love some guidance as to finding nice people who are, to use a term that was in a recent article of yours, DTF (Down to Fuck), but have that FFR (Feelings For Real) deal going on as well, and who believe in the importance of communication.

Since writing the column you refer to “Can I Be DTF and Still Respect Myself?” (Dec. 10, 2015) I’ve been thinking about this Tinderiffic tightrope millennials teeter on between casual sex for sex’s sake and the acknowledgement of feelings.

In “Can I Be DTF?” I encouraged the question-writer to continue to take pride in her pleasure-positive sex life while eschewing the idea that one must be void of all feelings in order to truly be DTF. In the end, I concluded that one can be both DTF and experience (and express!) FFR (Feelings for Real) simultaneously, but I continue to wonder how this can be incorporated into “Slutever Forever” sexual culture.

I’ve found one thing to be true of all sexual interactions: everything exists on a spectrum. Even in the case of DTF versus FFR. Does casual sex need to be no-strings attached? Can there be like one or two strings? Can our strings exist on a spectrum, too?…continue reading…

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Am I a Creepy OKCupid Troll?

It’s been a few years since I last got laid. Lately I’ve been trying to use OKCupid to look for a hookup. I also tried using Craigslist personals, but that didn’t go anywhere. While on OKCupid I email women asking if they want to chat, but I don’t get a reply in return. Many don’t even look at the message. I just don’t know what to do anymore.

I’m an introvert and never had that many friends so it hasn’t been easy for me. I used to go out to the bars locally or in downtown Springfield, but I usually ended up doing the driving and didn’t get to socialize much because I’m shy when talking to women.

Do you have any advice on what I could do?

Being a shy, introverted dude attempting to navigate the cocky, charming, testosterone-fueled world of modern hook-up culture isn’t easy. It sounds like online dating could be a really useful tool for you to use as it’s intentionally set up for people to hit on other people from the relative safety of their iPhones — no extroversion required.

However, though you’ve found the right tool to use, perhaps you just haven’t quite learned how to use it well. Just because I took my local sex columnist’s advice and bought a fancy new vibrator, for example, doesn’t mean I’m going to be having incredible orgasms if I don’t first learn how to turn it on, right? Same idea…continue reading…


IMG_8753I’m teaching a workshop this month!

Thursday, July 16th. 7:30-9pm at Oh My Sensuality Shop in Northampton. $12/seat. Limited seating. 18+. Purchase tickets & find out more details here!