The Art of the Fling

A no-strings-attached liaison can help you get your groove back — as long as you follow the rules.

By Sherry Amatenstein, LMSW

Three months after turning 40, I pulled the plug on a draining live-in relationship. After that, the last thing I wanted was to get seriously involved with someone new. But my niece’s Bat Mitzvah was approaching, and there was no way I could turn up at such a public family event alone. So I advertised for a date. The personal read: "GOT THE GIFT, THE GOWN; NEED THE GUY…"The guy turned out to be Jason — 38, cute and funny, but also dense, unambitious, and a self-professed porn addict. Not the kind of person I felt comfortable attaching to permanently, yet he proved to be a great Bat Mitzvah dance partner. It was our third date, and we ended the night at a sleazy motel doing the horizontal mambo. I thought it a perfect passionate interlude, only there seemed no reason to end it. We were having (safe) fun with no messy feelings hampering said fun. There was no commitment, no steady Saturday night dates, but we agreed that when one of us slept with someone else we’d tell the other. (He was a sleaze but an honest one.) Six months in, as I was finishing my Q&A Dating Book and asking myself what the heck I was doing as part of a dead end duo, Jason confessed he’d weakened, had gone to some X-rated club and had gotten it on with a waitress in the parking lot. Bada boom. End of fling. We kept in touch sporadically, but the main bond between us had been sex — so when that stopped, so did our "friendship." Yet this connected but not connected enough to really hurt liaison got me over the hump and to the point where I was ready for my next Great Love. Anatomy of a FlingA fling, aka the anti-Great Love, can be the antidote to associating love with pain. It is somewhere between a one-night stand and a relationship requiring mushy Hallmark cards. Just how does a strictly passionate, ongoing (for a while) pairing help a heartbroken woman heal? You stay in the moment and connect to your inner teen; the days when carefree wasn’t just a word, but a feeling. According to Donna Sozio, the reason Jason and I lasted so long is there was little tying us together beyond sharing fun times. Explains the author of Never Trust a Man in Alligator Loafers: "Compatibility ruins a fling." Sozio cautions, "Make proof positive he is either too young, too old, too broke, or too far away for you to ever consider actually having a relationship with him. Otherwise you run the risk of waiting by the phone wishing, hoping, and praying that your ‘fling’ will call."Buy Never Trust a Man in Alligator Loafers Many women in our demographic feel uncomfortable indulging in, as Ann Fry delicately states, "A f**k buddy." Fry, the creator of, an online resource for baby boomers, points out, "If you like sex and you’re not in a relationship, what are you supposed to do?" Divorced at 56 after a 28-year marriage, Fry, now 62, explains, "I’m not a one-night stand person, but right now I have a lover who is an ex-boyfriend." The pair are long-distance trysters, their occasional get-togethers fueled by "laughter and sex." Fry adds, "When I’m with him I’m crazy about him, and when I fly home I’m fine." It’s BoomerTime A fling at this stage in life can actually be easier than it was in your 20s or 30s, as the pressure of finding the father of your future children is no longer a factor. Robin Wolaner, 53 and twice divorced says, "Being with Mr. Right for Now is so much easier than obsessing over Mr. Right." Wolaner, founder of, a social networking community for the over-40 set, shares, "Men more than women on this site are frequently the ones interested in finding something serious." The relationship expert ponders the reason: "Perhaps it’s because boomer men know their ‘performance’ isn’t the instant success it used to be, so they want to make sure there’s a real connection before they make themselves vulnerable." The Ground RulesThe best way to emerge from a fling emotionally intact is to establish safeguards at the inset. First, be honest with yourself. Are you on the rebound, looking to show an ex who cheated, "See, other guys find me attractive!" — or are you secretly hoping that your f**k buddy will wind up proposing?And while the purpose of casual sex is to have purposeless fun, observe the most important rule of flingdom: don’t go out without your rubbers. You’re not just sleeping with your fling partner, but everyone else he’s slept with over the years. The third rule is to establish boundaries. Communication is crucial. What are or aren’t you to one another? In my case, Jason and I dated other people but were sexually monogamous. Deborah Moskovitch, author of The Smart Divorce, says, "You both should have the same expectations. Don’t expect to be wined and dined or to receive flowers the morning after. Know that he’s probably out there looking for a relationship. You might be his holding pattern." Meaning he’s not your go-to person if the roof leaks or for a Valentine’s Day date. A fling partner is not your emergency contact on medical forms. Unless you both decide that despite your best efforts you’ve come to love one another (hey, it happens!) and want to change the rules.The Smart Divorce Another biggie: Don’t feel obligated to dish to your entire social circle about your latest bedwarmer. Most friends will likely be nonjudgmental, but the decision to disclose is totally yours.Lastly, be attuned to when the fling has run its course. Moskovitch says, "This can sometimes be considered a post-divorce adolescent phase…somewhere to hang your hat for a while. It’s a great time to learn about yourself, what your needs are, and what’s important to you: sex, companionship, communication…." Once it stops feeling comfortable, it might be time to move on.The move may be to another fling, a period of celibacy, or a real relationship. In my case, shortly after Jason and I hung up our dancing shoes, I met my potential soul mate. Ted was everything I’d ever dreamed of — and he proceeded to break my heart. But that’s another story. When I look back on my six-month fling and remember the ways we opened each other (who else could have gotten me to like boxing!) I giggle. And that’s not a bad legacy for a ‘dead end’ relationship — giggles and fond memories. Do you have a tough question about dating or relationships?E-mail Sherry at and your question might be featured in an upcoming column.E-mail Sherry About Sherry AmatensteinSherry Amatenstein, LMSW, is the author of Love Lessons from Bad Breakups and Q&A Dating Book. She runs dating seminars around the country and does private coaching — not to help singles marry in 60 days, but to uncover their blocks. She has given relationship advice on the Early Show, Regis, Inside Edition, CBS News, VH1, BBC, and many other programs. Her philosophy is that the most important relationship you’ll ever have is with yourself.Schedule a one-on-one coaching session with Sherry Buy Love Lessons from Bad Breakups Buy The Q&A Dating Book Originally published on, January 2008.

First Published Mon, 2009-04-06 18:06

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