After a bad breakup and years of being single, I’m dating again — but only attracted to unavailable types

Dear Wayne and Wanda,

I was in a relationship for a long time and it ended badly. That prompted several years of me being very single and very disinterested in dating or even casually seeing anyone.

But I got through that and the past year or so I’ve been trying to get back into the dating scene, with some marginal success. I say marginal because it seems like I’m only attracted to and get involved with people who are emotionally or technically unavailable.

For example, I had a fling with a friend who was separated from his wife. It wasn’t serious — we met for drinks a couple times, ended up kissing one night, and he ended things. He and his wife have since gotten back together. There’s also a guy who travels through town on business. We’ve met up for dinner and drinks, flirty banter and some end-of-night make-out sessions, but I know it won’t go anywhere. I also went out a few times with a friend who recently divorced. I know he’s nowhere near ready for anything long-term, and it’s almost like we bond on the annoyances of being single and dealing with breakups.

A couple of my girlfriends are really pushing me to change my behavior. They say I’m only going with these kinds of options because my guard is up and I’m afraid to get too close. They might be right. But is that so wrong? I guess I’d just like your unbiased perspective on my situation. Thanks!

Wanda says:

I definitely won’t claim to be unbiased, as I myself have experienced that scenario where we hone in on a connection with someone — despite the fact that no substantive, enduring connection is possibly on the table. I concur this is often harmless. There’s no rule that every romance should be bound for cohabitation, marriage or some other form of long-term fidelity. As a wise friend once said, some love stories are short stories, but they’re still love stories.


Ah, but love. That’s where things get tricky. It’s all fun and free-wheeling when one keeps their emotions curbed, when you’re clear-eyed and clear-headed enough to remain detached and protective of that vulnerable inner core. But it seems a prevailing truth that even the most carefree no-strings-attached entanglements end up in a giant knot of confusion and hurt feelings should they continue long enough, because inevitably, someone develops deeper feelings, wants more, and ends up disappointed and rejected.

This romantic rut you’re in for now may feel and actually be harmless. You’re testing the waters, getting your sea legs again, finding your vibe, and having flirty fun along the way. But there will likely come a time that you do want more, and that’s going to mean wading into deeper waters where more serious potential partners await. Yes, these more intense couplings can also produce deeper senses of loss and regret should they come undone, but they also yield richer emotional connections and rewards.

Wayne says:

Your friends are wrong. If you had your guard up, none of those recent red-hot, red-flag romances you mentioned would have ever played out. If your guard was up, you wouldn’t be out there getting knocked on your ass again and again and again and still hopping back up off the mat for more heartache. If anything, you probably need to put your guard up a little (or a lot) if you’re really looking for something with more substance, seriousness and sustainability.

As far as I’m concerned, though, your approach to getting back into the dating game is admirable and even impressive. You’re putting yourself out there, meeting people, getting through first- and second-date conversations, sorting out what will and won’t work for you, and getting some attention and affection along the way. Plenty of lonely, desperate singles would take a little slice of that any night.

Now, if you’re truly ready to level up and settle down with someone long-term, you need to position yourself in a much different space. Get on some dating sites and get off the hook-up rollercoaster. When you see those red flags or old flames, run away instead of running to them. You put in plenty of time getting into a good space and understanding what you want out of life and love. And now you’ve had a stretch of dating to further confirm it. Go with that now, be true to yourself and what you dream of, and see where that takes you.

[After a cycle of unfulfilling relationships, ‘you have to teach people how to treat you’]

[My girlfriend is great, but her constant picture posts on social media make me question her motivation]

[Ask Amy: My ex won’t stop contacting me]

Wayne and Wanda

Wanda is a wise person who has loved, lost and been to therapy. Wayne is a wise guy who has no use for therapy. Send them your questions and thoughts at