Miss Information: Tips for sending nude photos and romancing longtime friends.

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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.

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