Tips for sending nude photos and romancing longtime friends.

Dear Miss Information,

Is it illegal for two consenting adults to send nude photos to each other? — Paranoid

Dear Paranoid, 

Nude photos of what? The City Comptroller of Philadelphia? Your next-door neighbor? Black-footed ferrets? Oh, you mean each other. Yeah, that's probably okay. Make sure you're both eighteen. Even though the age of sexual consent is lower than that in many states, the law treats sex differently than getting nude in front of a camera. You have to be eighteen for that. Of course that means that right now, a sixteen-year old who sends another sixteen-year old an explicit photo — say, via text message — can be prosecuted in some states for distributing child porn. Thankfully, there are people who realize how ridiculous that is and are working to get the law changed.

I wouldn't go doing this at work or the public library or even while housesitting at your best friend's place. Wait until you're at your home computer. No matter how good you are at getting rid of the evidence, there are geeks out there with data-recovery skills who are better. They probably know what's running through my head right now as I'm typing this. Speaking of risk, make sure you're prepared for what happens if you go the mobile route. No one ever plans on losing their cell phone, but it happens all the time. Lock your phone and make sure your email passwords aren't being saved.  

Now that I've said all that, go out there and have fun, Paranoid. Photograph yourself from the neck down if you're still freaked out, or put on a blonde wig and a pair of sunglasses. Make concealing your identity part of the sex play. 

Readers, have you ever had a nude photo session backfire? Explain. 

Dear Miss Information, 

I've been really, really into a guy for a couple of years — there's loads of chemistry and sparks between us whenever we get together and we're great friends. Even though I've professed my love and interest on several occasions via email (and he's agreed that he feels the same way, albeit in more obtuse boy terms), living in different cities, his girlfriend, and my inability to make the first move have kept me from jumping his bones. Now, we're finally close enough for visits, and his girlfriend is out of the picture. He's invited me to come and stay with him, and of course I'm super-excited at the prospect of finally making the jump from friends to lovers. But, with all of our professed theoretical mutual admiration for one another and our strong friendship, I already feel nervous about the approach. What's the best way to make the first move here? Hopelessly Devoted 

Dear Hopelessly Devoted, 

Don't do what I did, which is start crying while giving him a handy. Just like you, I had waited a long time for this. He was a great friend, the kind of guy who'd help you move into a fifth floor walk-up but never came off like an asexual puppy dog because he'd find a way to pinch your ass as you're halfway up the stairs. He also looked like a young Paul Newman, so you can just imagine… Anyway, like I said, I had built up all sorts of assumptions, despite going into it pledging the opposite. I thought I'd be cool. I wasn't. I figured since we knew each other so well and had already discussed the possibility of things turning weird, things wouldn't turn weird. Wrong again.  

Based on this, and based on everything else I've observed about friends-to-something-more romance, I hereby order you to do nothing to prepare. There's nothing you really can do, anyway. Getting sexual with this person is either going to feel strange, repulsive, or amazing. Maybe all three at once. It's like eating Marmite for the first time, or dropping acid. You won't know what it's like until you do it. 

The only pre-planning I'd possibly advise is to have a few ideas in mind for the venue. You want something low pressure, but not so chaste that it makes hooking up an unrealistic option. Low lighting and alcohol is always a good combo. There's also the tried and true movie night with the shared bowl of popcorn. Horror movies seem like the obvious choice, because you can pull the whole "Oooh, I'm scared!" bit and jump on his lap. Watch out, though. Sucking tongue when there's blood spurting in the background can be off-putting. When it's between Saw VI and a dull art-house flick, choose the latter. 

Dear Miss Information, 

I met a guy. He is not my usual type — he's divorced with three kids — but I thought I'd take a chance. We went on a date, and at the end of the night, he asked me if I wanted to see the view from his place. I was hesitant. He said that it wasn't like that, so I went to his place but left quickly so as to not give him any ideas.  

I gave him my number, and he asked me if I wanted to meet up again. We went out for dinner and drinks and then went back to his place. He was very respectful, but he did try to feel my breasts and I kept dodging his hands. I don't know why I did that. I would usually let that go but I didn't this time. We kissed and made out for a while and he dropped me off at 2:30 a.m. I felt something strange right away. I had a feeling I wouldn't see him again.  

I texted and didn't hear from him until Sunday night, when he dropped off his kids for the week. I sent him another text and got no response. I called and left a voicemail, and he never returned my call. I sent him a quick e-mail asking if we were still on for a pre-planned tennis date, and he sent me a blow-off e-mail.  

The saddest part is that I am regretting not letting it go further that night, even though he probably would have done the same thing. Please help me so that I don't do the wrong thing again! No Third Date

Dear No Third Date, 

I'm having a hard time seeing what you did wrong here. It sounds like the "To Put Out or Not to Put Out" dilemma is weighing heavily on your brain. Did you stop the makeout session because you truly wanted to or were you worried about going too far and having him blow you off later? What if you had given him a taste of the goods? Would he be your boyfriend now? Are you being punished for what some might call "playing games?"

Absolutely not, No Third Date. We all have our own sexual pace. We make adjustments based on external input and how we're feeling in a given situation. I know you would have moved more quickly if you had felt more comfortable with him, but guess what? You didn't. Your gut was shouting, "PLAYER ALERT, PLAYER ALERT!" and his actions post-date made good on that message.  

Now, maybe this is a genuinely nice guy who just wanted to get to the good stuff more quickly, but I don't know if I believe that. You went to his place on both dates. You made out with him until the wee hours of the night. It's not like you sat on the couch with your legs crossed quoting scripture. If he can't wait a tiny bit longer, either he's not that into you, or he's bad boyfriend material because he's too fucking impatient. The main takeaway: you did what was best for you. Don't regret it.

Have a question? Email Letters may be edited for length, content and clarity.

Commentarium (54 Comments)

Sep 20 10 - 12:40am

I wonder what it's like to eat Marmite after dropping acid.

Sep 20 10 - 12:46am

My advice to Hopelessly Devoted: Your first move is kissing him. Kiss him as soon as he opens the door. That's what I did with my long-time guy friend when we were finally both free and he invited me over ... and we've been married 7 1/2 years now.

Sep 20 10 - 1:19am
Amber Lamps

Hopelessly Devoted: take it easy. Just take it easy and everything will take care of itself.

Sep 20 10 - 6:42am
Lindsay L.

Nude pictures always get leaked!

Don't do it!

Sep 20 10 - 6:43am
Britney S.

You can't trust any dude to take nude photos of you! Trust me on this one!

Sep 20 10 - 6:43am
Pamela A.

And never let them video tape you!

Sep 20 10 - 6:45am
Tommy L.

Sex tapes with your partner are awesome!

Sep 20 10 - 6:45am
Nikki S.

@Tommy L:


Sep 20 10 - 6:46am
Paris H.

You guys are awful!

Sep 20 10 - 6:46am
Sasha G.

I love it when I'm photographed naked!

Sep 20 10 - 6:47am
Kim K.

What's the big deal if other people see naked pictures of you?

Sep 08 12 - 11:04am

would you like one

Sep 20 10 - 6:48am
Emma W.

As long as you keep your panties on it's no big deal.

Sep 20 10 - 6:49am
Dov C.

Girls shouldn't worry so much about showing off their bodies.

Sep 20 10 - 6:50am
Joe. F.

I think it's wild when girls let me take naked pictures of them.

Sep 20 10 - 6:53am
Rob L.

Just make sure she's at least 18 or that shit could haunt you.

Sep 20 10 - 6:54am
Miley C.

I think it sucks that you have to be 18 to send your bf photos of yourself. I so want to do it but totally don't want to get busted.

Sep 20 10 - 6:57am
Andrea D.

@Joe F. @Rob L @Tommy L @Nikki S:

Like all men you guys are pigs.

Sep 20 10 - 7:36am

My wife loves it when I take photos of her

Sep 20 10 - 7:42am
Tom C.

My wife keeps asking me to take naked pictures of her but I'm not that into it.

Sep 20 10 - 7:42am
John T.

@Tom C.

I know the feeling.

Sep 20 10 - 7:55am
Katie H.

I have the same problem with my husband. He says it's against his religion to take naked pictures of the opposite sex.

Sep 20 10 - 7:56am
Kevin F.

I've got some awesome pics of my ex!

Sep 20 10 - 8:03am
Jada S.

@Katie H.

Maybe he just needs to be audited again?

Sep 20 10 - 8:32am
Nicole K.

@Katie H:

My ex was the same way.

Sep 20 10 - 8:33am

There is nothing wrong with naked pics. There are pics of me out there that have never been leaked. Some taken when I was 19 and some when I was 27 (I'm 34). I love that there are these pictures of my body in its prime and I'm sure I'll love it more when I'm old. I trusted both guys and that's important. They have copies but I have the negatives...this is KEY. What is life for, if not living it?

Sep 20 10 - 9:14am

Hopelessly Devoted should accidentally on purpose drop a box of condoms in front of him. That's all the cue he needs.

Sep 20 10 - 9:44am

Cute comments. I'll just add that "legal" varies by country and subject matter.

Sep 20 10 - 11:25am

@bearman: I'm not sure one could handle even *look* at Marmite after dropping acid.

Neck down only on any naked photos. Who knows who or what you will be in 20 years. You want those photos with your face on them published in National Enquirer during your Senate confirmation hearings?

For NTD: There's no guaranty either way. I've had relationships go wrong after sex on the first date and after no sex until more than six weeks of dating. You did what you felt comfortable doing, and that's exactly what you should keep doing in each new situation. Be yourself and don't try to game the system.

Sep 20 10 - 11:55am
Justin T.

Trust is important.

I have a lot of photos of my first serious girlfriend. She wanted to remain a technical virgin - yes she was that innocent - so we used the photos as part of our "everything but."

My friends have begged me to show them to them, but I never would.

Sep 20 10 - 12:30pm
@No Third Date

I think "he's not that into you" is probably the main issue, with a dash of "he wants to find out if the sex will be any good before he invests any more time and energy in you". There are a lot of people out there who seem great on paper, but are mediocre-to-average in bed. And vice versa, too; you can have fantastic sexual chemistry with someone who doesn't otherwise seem your type. When a man (or woman) wants to get physical quickly, it's not necessarily just about getting laid; it's also finding out what sex with this person is going to be like. That's especially true if you're lukewarm about somebody, and it sounds like you both felt that way about each other, so no big deal really.

Sep 20 10 - 12:43pm

To Hopelessly Devoted,
Here's what you do; get totally wasted on the first night, go back to his place, and casually pull out one of your boobs. Don't say anything about it, put it away, then go to sleep. In the morning, pull out your other boob, don't say anything about, and put it away. Then go out to lunch, come back home, and make out with him.

Sep 20 10 - 4:04pm

Re. No Third Date: Maybe he sensed that the "divorced with kids" thing was an issue for her (which she basically admits) and decided it wasn't worth the investment to try and get her to be okay with it. That is, maybe it was less about her totally reasonable decision not to screw on the second date and more about what he perceived as the underlying reasons for her choice. That said, I have no idea who this dude is--maybe he's just sulking that he didn't get laid immediately.

Sep 20 10 - 4:45pm

No Third Date: I have a woman friend going through exactly the opposite situation right now: he's not calling back.. did she let too much happen too soon? It sucks either way, but I think there's a real danger in over-analyzing this stuff. There are a million reasons people don't click. It sounds as if you had reservations yourself. Just chalk this one up to incompatibility.

Sep 20 10 - 5:03pm

No Third Date: Some guys (like me) expect sex in a romantic relationship. You made it clear to him that it that he was wasting his time if he wanted that kind of intimacy. I have kids--and I don't go for "playing and hoping". If it's just hope, then I'll move on. Good for him for saying "no", and good for you for moving on. You'll find someone who matches your pace...

Sep 20 10 - 5:25pm

@P - are you kidding me? Most adults expect sex in a romantic relationship but ditching someone after 2 dates for not putting out, especially without even talking about it? Good luck getting quality if that's your plan!

Sep 20 10 - 6:45pm

Meh, I could go on a 10 dates and not need sex still. Don't get me wrong, I love sex, my last relationship had so much it became unhealthy, but passion makes sex so much better imo that if that level isn't there yet, I won't try too hard to pursue sex...

Sep 20 10 - 7:28pm

Yeah about those nude pictures, they always get showed to friends. I have seen guy friends and girl friends naked pictures before. Those pictures are going to get around.

Sep 20 10 - 7:29pm

that was supposed to be pictures of their naked girlfriends.

Sep 20 10 - 9:51pm

Naked pics make me worried. Of course I always trust the guy at the time, but I don't keep in contact with all my exes. The guy I'm dating now has pics of me buried deep in his hard drive, and I'd never be able to delete them off his computer because it's password-protected. It's all fine and good for him to have pics while we're dating, but he admitted to me once that he still had pics of his most recent ex too, which was skeezy. He said he deleted them, but again there's no way for me to know for sure because if they are still there, they are buried deep and password-guarded. So I worry what will become of my pics if/when we break up.

Sep 20 10 - 10:26pm
Ryan S

@NoThirdDate -- I'm sure the guy just wasn't interested. I've been in the same situation, and the reason I ended it was because I was no longer interested. It would have been the same if you slept with him. Regarding Fotos -- I had fotos of my ex that I deleted when we broke up, so not all fotos get leaked, but of course they can be. @Hopelessly Devoted -- I like @betty's suggestion. From the sound of it, he's into you. I also like @SirWalter's , but I'm not sure how well it would work. : )

Sep 20 10 - 10:30pm

Who cares what he's thinking? Were you true to yourself? If you were playing a game, and you got played, then you're right to be upset. Stop playing games, then- just live for yourself and when you meet the right person you'll have the chemistry and the ability to wait until you're both ready.

Sep 20 10 - 11:04pm

excellent advice, especially on the last letter, from Miss Info.

The line "either he's not that into you, or he's bad boyfriend material because he's too fucking impatient"

is dead-on balls.

Sep 21 10 - 5:29am

@hopelessly devoted: like betty says-- kiss him right off when he comes in and get it over with. or wait and just do it by surprise while sitting around talking, but don't let it drag out. It will reduce some of the tension and make the second kiss a lot easier.

Sep 21 10 - 8:42am

@HopelesslyDevoted: as bd says, don't drag it out - but give yourself a little time too; while there is no right time to make a move, there are some definite wrong 'uns. I've been through this recently (we got together just less than a month ago) and it was the day I climbed a hill with him and realised the reason I felt sad all day wasn't because I was with him, but because I wasn't holding his hand, that I made the move. Not sure that explains it. But anyway, it was amazing. :D

Sep 22 10 - 9:26pm

To Hopelessly Devoted: How about you go for a guy that doesn't have a girlfriend?

Sep 24 10 - 1:31am

Any man who dumps you because you wouldn't give it up on the second date is a scumbag, you're better off without him. Quality guys will respect a woman's boundaries. The added plus for the guy is waiting for the girl to make up her mind. You'll know she's doing what she wants to. My dad said one thing to me about sex when I was 13. Whatever you're doing, be certain the girl wants to as well. NEVER do anything against a girl's desire.

Sep 24 10 - 9:46am
David B.

The important thing to remember when sexting is to erase the images and texts from your cell phone.

Sep 24 10 - 9:47am
Tiger W.

@David B.

You got that right!

Sep 24 10 - 9:47am
Victoria B.

@David B

You bastard!

Sep 24 10 - 5:39pm

Foamgreen has it right. I was reading that thinking, "what do you mean, "the girlfriend is out of the picture." Because that's not the same as saying "He's finally single!" and it's a slip I find suspicious...

Sep 27 10 - 11:35pm
@Andrea D

I THOUGHT YOU WERE DEAD! ...but then I thought tupac was dead too hahaha

jokes! Whoever you are, you are brilliant.

Oct 06 10 - 2:03am

Aww Erin, I'm sorry. Hand jobs are so sweet to me for some reason. I don't know why but they can get mad emotional, I think because you're both so visible to each other...

Oct 06 10 - 2:04am

@ThatKindaGirl "I have the negatives". Now that is a blast from the past if I ever heard one.