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Betting Enough to Break Even

In relationships, how should women know when to hold out, give in or let go?

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

Jennifer Fisher (Editor) January 09, 2012 at 03:56 PM
My grandmothers are pretty silent on the dating front. But one friend's grandma always tells this story: she was dating a guy she didn't really like, and he gave her a pearl necklace. They broke up, but she made sure to keep the necklace. Her lesson: "Girls, always keep the pearl necklace."
Jennifer Fisher (Editor) January 09, 2012 at 03:57 PM
When it comes to marriage, however, one of my grandmothers claims she was proposed to 13 times. We'll never be able to fact check that story...
Dafna January 09, 2012 at 07:28 PM
I'd love to see what you have to say about cyber-dating. Personally, I think it sucks, and is an easy way for people to be even less honest about themselves (then they would be in person). I have been on these sites for almost two years, with absolutely no prospects. I have to say in regards to this article, that my grandmother has always said the same thing (the guy should love you more than you do for him). I think she is right, seeing that I also am the girl who takes a connection over stability (but really want both). Maybe we can't have both, but I just don't know how to do that.
Cyndi Gage January 09, 2012 at 08:48 PM
My husband and I met on-line in 1995 in an AOL Baby Boomer chat room. It was a group of people from the same age group and mostly of the same income group (it wasn't cheap to chat online in the old days). In the beginning most people were who they claimed to be. More than a few of us have married the person we met there and still remain friends with others we met there. I can't comment on actual 'dating services'. Successful relationships seem to be those people who share the same core values. Be up front with who you are and don't pretend to be something that the other person wants. You must be secure in who you are and what you want before you can attract a person with those same qualities. And never, ever settle.
victoria smith January 10, 2012 at 01:17 PM
My Mother's sister, my Aunt who lived with us since I had been a baby was a prime example of "never settle" She was a beautiful woman, intelligent, artistic, independant and quite the world traveler. Never once did she complain about not having married. Her only regret was not having children. Her men companions were always well to do business men that wined and dined her and presented her with esquisit jewelery. I loved listening to her stories of where she had been and the parties that she attended. I asked her one night when she had come home from a dinner fundraiser at the Art Institute if "he was the one?." She looked at me and said" " I have dated lots of men and all of them were charming, witty,well situated and were fun to be with, but none of them were someone I want to get old with. None of them kept those butterflys." I thought about it for a minute and asked "No prince Charming on a white horse?" "No, no Prince Charming on a white horse, but I am ok with that because I like my life and I like me and if this is the way it is going to be I am happy with that. Never settle because you think that you have to in order not to be alone. You can be just alone in a marriage if it is not right." Well, she never found her knight in shinning armor, but I do believe that she really did love her life and the all the suitors I am sure loved her as well, but as she said, "You don't have to settle." I am sure that her way of life was not the "norm" , but she liked it.

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