How to make Casual Flings Work


In the last few weeks, we’ve talked about how to make friends with benefits, long term relationships and open relationships work. This week, we’re all about casual flings – well, at least in the sense of trying to help you figure out how to make them work for you rather than against you should you choose to indulge in a hook-up:

1. Know thyself. The saying has been attributed to many great thinkers, including Socrates, and it rings true here too. Sex and the City, to some extent, glorified casual sex arguing that yes, women could have “sex like men”. But not all women – or men, for that matter – are built for casual flings. Some are, some aren’t. Knowing which type you are is half the battle. Being true to yourself is the second important half. If you like no-strings-attached sex or make out sessions, that’s a good thing to know about yourself so that you can just admit to liking it rather than pretending to your friends that you were tipsy and didn’t know what on earth you were doing (unless, of course, the latter is true – then watch your drink intake, my dear).

2. Come prepared. If you’re going to indulge in casual encounters, try to reduce your risk of unintended pregnancy and infection to the best of your ability. Keep several condoms on hand and preferably different types – after all, condoms do break and some people prefer different kinds than others. If your guy doesn’t like what you’ve got, hopefully he brought his own. Otherwise take a rain check or kiss all night instead. You might also want to carry a few tiny sized pillow packs of lube in your purse, too, to make sex more comfortable or pleasurable (especially if it’s a tight fit). And don’t forget to use a reliable form of birth control – preferably in addition to condoms. Hormonal contraception (such as the pill, patch, shot or ring) tends to be more effective than typical condom use but they don’t offer protection against infection. Thus, a two-pronged strategy (birth control plus condoms) may be a good bet. Check in with your healthcare provider to explore your birth control options.

3. Safety first. As fun as the phrase “casual encounter” can be to use, please for the love of SATC’s Samantha do not randomly hook up with people you “met” over the internet such as on Craigslist or a dating site. Always try to meet strangers in public several times before going anywhere too private with them. And when you are ready to go somewhere private with them, make sure that a trusted friend or family member knows where you are and who you are with. Print out copies of their profile and/or your email exchanges and leave them on the counter or in a desk drawer. Give your best friend their cell phone number and/or email – just in case. If your fling is someone you met at a bar, make sure your friend has their contact info. Some people seriously insist on seeing the person’s driver’s license (and showing it to a friend on the neighboring bar stool) before going home with them. Follow your gut instinct and keep tabs with your friends for the best odds on your personal safety. Oh, and make sure not to give out your home address to people you don’t know. It’s easy enough to communicate through Facebook, email or texting.

4. Have realistic expectations. Unless you are one of those rare women who can orgasm at the drop of a hat, or has perfected not only their technique but their comfort giving clear instructions to a partner, it may be that sex is less than fabulous during a one-nighter. That doesn’t mean it’s going to suck, but it does mean that having realistic expectations about what is or isn’t likely to happen may help you to better enjoy it. For example, if you were out drinking heavily then a guy may have a higher chance of having erection problems. Performance anxiety can impair orgasm and contribute to premature ejaculation, too. And women’s orgasm? It’s far more likely with a regular partner. That doesn’t mean that casual flings with new lovers can’t be hot – what they lack in practice they can make up for in novelty and newness. It’s just a matter of opening yourself to the many possibilities that await you.

Although casual flings aren’t for everybody, many people try them out while they are in search of a longer term relationship or in between lovers. If it’s something you’re curious about, I hope these tips with help you to proceed with confidence and pleasure. And don’t forget to pack contacts or sample sized toiletries in your purse if you’re planning to stay over.

Related MSP posts:
- How to use vibrators to boost desire and make it easier to orgasm
- Masturbation sleeves: more cushion for your pushin’
- Tips for men on how to shave their pubic hair 

[Originally published in my weekly column at]

About Dr. Debby Herbenick

Dr. Debby Herbenick

Dr. Debby Herbenick is a sex researcher at Indiana University, sexual health educator at The Kinsey Institute, columnist, and author of five books about sex and love. Learn more about her work at