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The V-Spot: Healing an Ex-Shaped Hole in the Heart

Dear Yana,

It’s been over a year now since I got my heart stomped by my ex-girlfriend. We were together for 11 years and our relationship ended very badly. Even after such a long term relationship,

I’m still pretty young — in my mid-30s — and I’m pretty sure I’m a catch. But, every time I go out with someone from OKCupid, I never want to see them again. They all seem totally unhinged and just not like anyone I would want to date, casually or otherwise. I’m not even sure that I can do “casual,” now that I think about it.

But I feel like I should be out dating people to see what else is out there and fill this hole in my heart that seems like it’s just never going to go away. How do I let the dating duds down easy while not being a total asshole? What if my heart NEVER heals?

Oh, Holey Heart

 

Dear Holey,

The good news is, heartbreak does heal. Well, at least the agonizing part does. When it comes to long-term loves like the one you describe (an 11-year relationship before you hit 40 runs you through some critical life developments!), the heal time will certainly feel slower. Plus, people’s major loves in life often forever linger. And that’s normal.

The first thing to do, HH, is to stop looking for a replica of your ex. And I don’t mean physically, but more in the way that your specific relationship made you feel when you were first meeting in your 20s, deepening your connection towards your 30s, and whatever you were desperately trying to save towards the end.

A new relationship will not scratch the same itch in the same ways and you as an individual are not the same person you were during the relationship with your ex. Open yourself up to new possibilities of what makes for an attractive partner in the here and now rather than trying to fill the ex-shaped-hole in your heart. Trying to fit an OKCupid date into that shape will prove to be fruitless, frustrating, and a painful reminder that no one will be your ex. And they won’t! And that’s okay. But fighting it makes the healing harder.

Instead, find a new lil’ neighborhood in your heart and let your casual dates hang out there — see if they like it, see if you like it, see what parts of you they challenge, excite, or even point out to you for the first time ever!

Rope off a little place where casual dates are allowed to roam and if you find someone that sticks, you can expand the territory…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!