He's an ex-convict. She's only 27 and has already been married 11 times. The What the Hell Was I Thinking Fling is dangerous, thrilling, and someone you'd never see yourself dating.

 

Except this once.

 

Dating coach Brett says, "Chalk it up to experience. You can learn something from everyone -- even if it's what not to do..."

 

The downside (other than possible jail time)? Brett says, "The What the Hell Were You Thinking flings often give you a sense of regret that you can't shake off for quite a while. Make sure you don't beat yourself up over it and remember that it was just an experience that helped you grow and change -- plus you'll know what not to do (or rather, who not to do) next time." 

 

 

He went to Harvard, you went to Ball State. She listens to NPR, reads Voltaire and Jean-Paul Sartre, and you watch Wipeout and listen to Howard Stern. The intellectual fling is good for you because it challenges your belief system, makes you defend your thoughts and positions on world issues, and maybe, just maybe, exposes you to ideas and experiences you hadn't considered before. Like experimental community theater. Or 7-hour discussions on existentialism. The good news is that you'll never run out of things to talk about. The bad news is that you may wish you would.

 

Says Brett, the benefits of the Deeply Intellectual Fling are pretty, well, deep. "You learn new things, expand your mind and generally feel like a better person for it." The drawbacks? "Talking about politics and the property market gets a tad boring when there's Gossip Girl to watch and nails to be painted."

 

Dating Expert Brenda Della Casa agrees, "The brain is the least-used sex organ and when it comes to hot flings, a mind really is a terrible thing to waste. A strong intellectual connection creates a sense of unity and bonding and can lead to passionate debates and flirtatious witty banter.  As long as your attraction for his body is as powerful as the attraction to his brain, the only downside a fling like this could have is if an intellectual competition starts brewing and someone switches from complimentary to condescending."

 

 

You're covered in banana pudding, wearing a blindfold and trying positions you never knew existed. Congratulations, you've just nailed your Wildest Sex of Your Life fling, and you'll probably end up replaying this day/week/month until you die.

 

Della Casa says, "There is no denying great sex can be intoxicating but it's important to recognize the difference between a fantastic sexual connection and a great emotional one. Having a fantastic sexual fling will likely allow you to explore sides of yourself, your fantasies and the ways in which you carnally connect with another without the pressure of "what does he think of me" woes. 

 

The drawbacks (besides chafing and running out of condoms at 2 am?)

Della Casa says, "The downside comes about when one of you thinks it's just sex and the other thinks it is a whole lot more. The need to protect your body is obvious but don't forget to protect your heart by being open and honest about who you are and what you're thinking and expecting them to do the same."

 

 

It didn't work out the first time, but one or both of you still carry a torch. You run into each other at a party or bar and wham! Before you know it, you're half-naked, making out like crazy on the couch. Things go great for a few weeks or months, and you can't believe you ever broke up. Then, something triggers an argument, and you're right back where you were eight months (or eight years) ago.

 

Says Della Casa, "Ex-sex is seductive because it's familiar and often more comfortable than sex with someone new, but the drawbacks can be downright devastating.  I don't know too many couples who have broken up who can hop in the sack and come out from under the covers with them both glowing and emotionally detached."

 

She adds: "Turning back the clock places you back in a broken relationship and may very well rip open old wounds or have one of you feeling things the other has locked away in history.  The best thing you can do for yourself is to write a new chapter with new characters instead of trying to re-write history."

 

The most important thing to remember about summer flings is that they're not built to last. The key is to enjoy them for the frothy delights that they are, without worrying about tomorrow.

 

After all, that's what summer flings are all about: Enjoying one day in the sun at a time.