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

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. Adjust your expectations to mitigate the letdown you feel when they don’t fit into the your-ex-shaped-heart-hole because again, remember: they won’t! That wound will close with time-related organic processes like space, acceptance, learning, processing, self-reliance, and readjusting.

OKCupid can be great because it allows you to set your boundaries clearly. Let prospective dates know that you’re looking for casual connections with the possibility for longer partnerships if it feels right. Enjoy what casual dates have to offer rather than resenting them for what they’re not. Be clear about what you want without making it too personal — “I don’t think the chemistry was right for me” comes off a little differently than “YOU SEEM UNHINGED. GET AWAY FROM ME!”

Or, give yourself permission to heal like molasses, put all dating on hold, and nurse your wounds. A broken heart can often act like a broken ankle — you might be able to walk on it after the cast comes off, but running a marathon might very well re-injure. Don’t push it, and listen to your body — especially that particular organ beating in your chest.

Yana Tallon-Hicks is a relationship therapist, sex educator, and writer living in the Pioneer Valley. You can find her work and her professional contact information on her website,