Ask Polly: I Keep Drifting Into Meaningless Flings!

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Dear Polly,

I am desperately seeking stability: I’m 29 years old, unemployed, and a juggler of multiple romantic relationships (entanglements?). I am having difficulty staying afloat (paying bills, student loans) and not turning into a ball of despair and self-pity. I attended graduate school and moved several times across the country in pursuit of a career that I eventually found to be unfulfilling. Thankfully, I’ve found a vocation that appeals to me and started taking classes to refine skills and start building a network. I got a volunteer gig that allows me to apply my new skills and meet like-minded people. I have a regular babysitting gig that sort of (read: barely) helps prevent me from annihilating my savings quite so quickly. Though I like babysitting because it pays as much as working at a coffee shop and only requires me to deal with one human being at a time, witnessing others’ apparently forward-moving lives and domestic satisfaction makes me feel inadequate.

I recently wrote a long email to a friend abroad, and I later realized that the majority of the text was dedicated to the multiple men that I have been dating. While there were other things going on in my life, the thing that filled my headspace was romantic affection and sex. One of the men — to whom I feel the most attached — just informed me, at the end of a date, that he was going to talk with his ex about getting back together when he returns from a trip in a few weeks. I had a feeling of déjà vu: A while ago, a different man broke up with me (at the end of a date) by telling me that he fell in love with someone at a wedding and was going to marry her. (I’m glad that didn’t work out, but it still hurt! And they are still married, apparently.) I think I would have preferred this man ghosting me rather than telling me that I’m not as good as his ex, to my face, and then asking me for my thoughts. Though my mind swelled with anger and resentment, I could only mumble, “Well, you were in a very long relationship with her, and in retrospect, you were probably never over her in the first place,” and then ask if he still wanted to have sex that evening. I felt better after the sex, and frankly, I feel better after sex in general — the sense of well-being and of feeling desired is soothing to me, however brief. It helps to make me feel indifferent about emotional agony, enough to help me get back on the subway without having a breakdown.

Despite my excitement and passion for what I hope will turn into a career, I am ashamed by my unemployment and general insolvency, and disappointed by what seems like a stream of rejections from prospective employers and men. I am afraid to ask for help from my family because I worry that their assistance will become material for guilt trips later on. Basically, I don’t take rejection well, I’m bad at asking for help, and I have difficulty trusting people. Also, several men I’ve dated have expressed surprise at the fact that I’m seeking a committed relationship at all because they assumed that I had too much going on to want anything more than a casual thing. And, to make matters worse, I recently moved states and I am on the wait list for a new internist — my meds have run out, and I’m trying to find a therapist, and I feel as if I’m losing control of my life. I’m getting tired of swimming in choppy water, and I realize that I’m using relationships and sex as pieces of driftwood to which I can cling (a strategy that does not lend itself well to good relationships). There are days when I hate myself and resent my inadequacy and worry that no one will love me because I reek of failure. In public I don’t think I come off as despairing (people seem to find me cheerful and fun), but in private I have a very hard time dealing.

Stranded at Sea 

Dear Stranded at Sea,

As long as you treat sex as a form of reassurance that you’re worthy of love, you’re not going to find the emotional connections you crave. If you try to seem cheerful and fun and you fall into bed at the slightest sign of interest, all the while masking a deeper well of fear and despair, healthy men are going to sense (correctly!) that you’re deeply conflicted and insecure and prone to abandoning your own best interests in pursuit of approval.

This doesn’t mean you’re bad or unstable or even that you reek of failure. The only thing that’s really wrong here is the disparity between the person you’re pretending (and trying) to be (unconcerned, upbeat, detached) and the person you really are (serious, complicated, occasionally melancholic). The short answer to your current troubles is simple: Instead of assuming that men will never love the woman you really are — a pensive, uncertain woman at a crossroads — you need to assume that someone will love that woman, and you need to be the first person in line for that job. You need to struggle mightily to give yourself love instead of hating yourself. Maybe you don’t love yourself right now because you don’t love cheery, upbeat fakes who secretly fear rejection. Maybe you love women who tell the truth about what’s real for them. So tell the truth, be the woman you really are, and love that woman intensely.

And by the way, the man you want in your life doesn’t love cheery, upbeat fakes, either. He loves women like you — the you who’s hiding behind all of this bullshit.

Draw a line in the sand today. No more begging for sexual scraps and pretending that they’re sustaining you. Stop telling yourself that you can at least hold yourself together if some indifferent dude throws you a bone occasionally. Every time you settle for leftovers, you’re telling yourself that’s all you deserve. The second you resolve not to act like some kind of emotional beggar who’ll take whatever she’s given, your whole world is going to change. Men are going to treat you very differently; women are going to treat you differently; the whole world is going to treat you differently. But most important, YOU WILL TREAT YOURSELF DIFFERENTLY.

Imagine for a second NOT shifting into this clinically detached state when you’re faced with rejection. Imagine NOT asking for sex one more time. Imagine expressing your emotions, then stating your values and your desires out loud, and then leaving. Imagine walking to the subway and feeling proud of yourself for standing up for yourself. Imagine feeling strong and beautiful on that walk.

It’s time to stop opening yourself up to rejection by strangers and acquaintances and guys with tastes and preferences that have no bearing on your life, that say nothing whatsoever about your worth as a person. Today you resolve to hold out for a love that feels purposeful, pure-intentioned, and passionate. Today you resolve to start by giving yourself that kind of love. I know it sounds cheesy and gross, but it’s transformative to care about yourself for a change.

Then apply the same powers of imagination to your career. Give up this refrain that you’re adrift, you’re a loser, you’ll fail at everything you do it bears no relation to reality. The fact that you lump together romantic and career disappointments, summing them up as a very personal message about your worth, is a testament to your tendency to globalize and overgeneralize about your problems instead of thoughtfully analyzing distinct choices you’ve made and will make. As long as you indiscriminately treat every romance and career opportunity as a countdown to rejection, that’s what it will be. The fact is, you’re doing work that you care about, and eventually you’ll get paid for it. Investigate new ways to make money. Find a psychiatrist who can write you a prescription for your meds immediately, and THEN take more time to find the perfect therapist.

Stop acting like everyone in the world has some secret power that you lack. SO many of us feel that way at your age, and it’s such a mindfuck. You don’t have to wait for their permission to move forward. YOU ARE THE DECIDER. This is your life! Make a commitment to yourself, to love and protect and honor yourself from this day forward.

What does it mean to own who you are? It means you occupy the world in a new way. It means you have a voice and you’re not afraid to use it. It means you know how to state your values out loud, without smiling apologetically. I have only recently learned not to compulsively apologize for everything I do. I don’t smile and try to take up less space anymore. Sometimes a woman needs to practice serving up a blank expression to the world, a look that simply says, I am here. I am not here for you. I am here for me. Deal with it.

Relaying the little ups and downs of a million affairs via email is sometimes a way of being seen and heard, but it’s also a way of moving through the world like a giant question mark. You’re breaking down the little dramas of your life in order to get reassurance. It’s understandable, but right now you need to learn to reassure yourself. Step back from your compulsive, minute-by-minute distractions — and sexual intrigue constitutes the same kind of fix — and connect with who you are. Center yourself and push away the voices that say you’re worthless. Insist on a different story. Those voices — where did they come from? Why are they so relentless? Tell them to fuck off until you can’t hear them anymore.

You don’t have to be cheerful or indifferent. There’s no special victory there. You can admit that you feel like a failure. You can admit that you feel stranded and lonely. Go ahead and fall to pieces. It’s not that bad, you’ll see. And when you’re done, rescue yourself.


Order the new Ask Polly book, How To Be A Person in the World, here. Got a question for Polly? Email Her advice column will appear here every Wednesday.

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Ask Polly: I Keep Drifting Into Empty Flings!