Betting Enough to Break Even

I can’t count how many of my friends have been in ‘conditional’ relationships with guys. You know the kind—he’s not quite emotionally available, but more than happy to roll through the aisles of your heart, filling his cart up with your compassion, understanding and feminine energy like a frenzied contestant on Supermarket Sweep

Just last week I had dinner with a college friend who told me about a summer love that she recently cut off because the dude wasn’t over his ex (and, apparently, still hanging around with her).

When she realized—after several months of his empty assurances—that there was no chance of a real, committed relationship with this guy, she finally mustered the strength to cut ties. Why do we go along with these arrangements in the first place? Smart, beautiful, got-it-going-on girls, settling for guys who string them along and won’t go all in (and, in many cases, aren’t even a prize to begin with).

Truth be told, I’m President of the above Club. Like many women, I seem to be attracted to the men who make me work for it, enjoy all I have to offer, but don’t put much in themselves. , a reader mentioned something in the comments about feeling secure with a man versus feeling a real spark. The latter, as our dear reader pointed out, often ends in heartbreak.

Over the past few weeks, I’ve spent my free moments between holiday craziness thinking about my online dating profile (thanks for all the feedback, I’m joining Match and JDate), past relationships and the kind of guy I’d like in my life moving forward.

Thinking about my friend—and my own involvement with guys who can’t commit—reminded me of a single piece of advice my grandmother shared just around the time I started really noticing boys. 

“Never chase a man, it just doesn’t work,” she told me. “Marry a man who loves you more than you love him.”

Sitting in her living room, eating spice drops out of a crystal bowl that never seemed to go empty, I was stunned.

Was that true? At 13 years old I hadn’t even considered the notion that marriages could hold imbalances like that. At the time, I mostly dismissed the advice as the well-meaning but out-of-touch sensibilities of an older generation with old-fashioned ideals. But 15 years later, I’m wondering if there was something to my Gram’s advice.

One of the and sharing my sometimes-nutty but always-churning internal dialogue with you all, is that I have the opportunity to gut check.

I’ve always been a heart-on-my-sleeve kind of girl, putting in my all and holding on to men I care about, even after the relationship has well passed its sell-by-date. I’ll admit it: I stay at the party too long.  

I’m not quite ready to sign-off on my grandmother’s marriage mantra but I am approaching the men that make my heart go pitter-patter with a lot more cynicism. I’d still like to think there’s a guy out there who can give me butterflies and also be someone I trust not to mess with my heart. But the fairytale balloon of love and relationships I toted around as a little girl is starting to lose air.

Maybe Gram was onto something. At the very least, I know I’d rather not chase someone who’s not chasing me, too. I’m venturing back out there with an open mind, but protected heart. Maybe your insight can better light the rocky path?

As I jump head first into the online dating jungle, I’m hoping you’ll share your stories, experiences and nuggets of wisdom in the coming months. All you readers out there in Patchland, I want to hear from you! Whether you're single, dating, married, or divorced, sound off in the comments below or share with us on Facebook. 

Up Next: Decoding cyber dating. Tune in Jan. 23.