Photo of Jennifer Aniston & John Mayer, in happier times, via Splash

This week's bucket list edition goes out to reader Anna, who writes: "My boyfriend and I would love to have sex in [his parents'] pool at home. Should we do it at night when no one's up but it's dark, or in the day when no one's home (possibly--or the neighbors)? And how do we use a condom in the pool?"

1. Unless your boyfriend's pool has a motion detector, we recommend doing it at night, especially if he has nosy neighbors.

2. Then again, if you're busted "swimming" in the pool at night, be prepared for everyone to know exactly what you were doing. So keep the noise level down and wear your bikini top, just in case.

3. For anyone out there whose boyfriend doesn't have a pool, you guys do all know that it's illegal to have sex in a public pool, right? Not to mention gross--and bad manners to boot. Good. Just wanted to clear that up. (We're assuming the ocean is illegal, too, but if it's totally deserted and you're sure you won't get busted...well, you didn't hear it from us, but we reckon etiquette would allow that, even if the law wouldn't.)

4. You will need lube. Lots of it. The water will wash away your natural lube as well as any lube on your condom. And man-made water-based lube will wash away, too, so you'll have to use a silicone-based lube like Eros Bodyglide. (We know what they say about oil and water, but oil-based lubes aren't safe to use with latex condoms.) Silicone lube needs a good dose of soap to make it go away, and that's a good thing when it comes to pool sex. Lots of lube will also help ease the irritation factor, though if your vagina is a sensitive little bunny, be warned that underwater sex may leave you a little, well, irritated. (There's also a small chance that the chlorine could give you a yeast infection. Life's a bitch that way.)

5. Okay, here's the deal with condoms: the manufacturers don't test them (or guarantee them to work) in water or in pool chemicals. The condom might break, and water could get inside the condom and cause it to slip off. So if the condom is your only method of birth control, then we can't in good faith recommend you do this. And if you haven't been tested for STDs together and know each other's sexual histories, then we definitely can't recommend it.

6. Speaking of back-up birth control, it should be something that won't be affected by the water, i.e. the Pill or an I.U.D. or the rhythm method will work, but spermicide, a diaphragm, or the Sponge won't.

7. If you do use a condom (and you swear you have a back-up method of birth control and you've had the whole STD chat), then he should put it on before you get in the water. And you should know that if he gets a little soft at any moment (if, say, the pool is unheated) then the condom is even more likely to slip off.

8. That all said--and thanks to About.com for this excellent suggestion--a female condom is much less likely to slip out underwater. Again, just be sure to insert it before you get in the pool. (This will also save your boyfriend from having to cross his parents' patio at night with a raging boner.)

9. Underwater oral is a neat party trick, but we don't think that's going to get anyone off. (Though it will give you something to do if his parents wake up and you have to hide underwater until they've gone.)

10. Finally, and most importantly of all, don't forget to take the condom with you. Because a floater of the latex variety is about a million times worse than doodie in the pool.