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
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.

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