Penelope Trunk founded three startups, including Brazen Careerist. Her career advice runs in 200 newspapers. Inc. Magazine called her "the world's most influential guidance counselor."

Forty year olds can sext, too! As Rep. Anthony Weiner's Twitter scandal grabs headlines, career-advice blogger Penelope Trunk explains why she let her own inhibitions down and learned to love sharing nude photos and dirty text messages.

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Three years ago I divorced with no clue as to how people date. I think I probably never had a clue about how people date, because I have Asperger Syndrome. This mental deficit means that I am bad at understanding social rules, since most are not written down. And I’m bad at understanding nonverbal communication, which is basically 100 percent of the real communication of dating.

I am very easy to get into bed because the dance people do before getting to the sex part does not make sense to me. Here’s a post where I describe what it’s like to have sex with me. But here’s the bottom line: once I’m there, clothes off, I’m a lot of trouble. Because there is not really a way to get from clothes off to bodies connected without a sort of nonverbal dance of pleasure. Or displeasure. Or something.

So I decided that I have two things going for me: I am usually the smartest woman a guy has ever dated. This gets me through the terrible conversations. The guy thinks to himself that he knows I’m not stupid, so maybe he is stupid and that’s why I sound stupid. Really. This is what I think they think.

The other thing I have going for me is that I have a great body. I used to play professional beach volleyball. Sponsors paid to put their name on my butt. I signed autographs in a bikini. So each time a guy thinks that I’m too much of a whack-job to put up with, he remembers how hot I am, and he keeps going.

The problem is that 15 years and one divorce later, I was not sure I had the body to pull off that delicate balancing act. I worried that as I get older, I get more quirky and more saggy, and it’s a bad combination for dating.

I did a lot of research about breast lifts and tummy tucks, while I wondered, can you date a guy if the first time he sees you is when you have post-breastfeeding breasts. What if he’s never even seen that? It’s not fair. I want breast implants.

That’s what I told myself. And, as you know, divorce is a tough time, and I was able to pretty much distract myself by obsessing over the sagginess of my breasts. And, also, is it fair to wear a push-up bra? Is it misrepresentation? These are things I had to find out.

In the meantime, I have a very popular blog. And as soon as I announced I was getting a divorce, my blog became my personal dating site.

One fun story is the 25 year old. He himself is not that interesting. In fact, if you are in your forties and you date a 25 year old, it’s safe to say that the kid is going to bore you to death, but it sure was fun to try that out. I’m not going to tell you about all guys. Although the alcoholic who had the same divorce lawyer that I did appears to still be available and he’s very rich, so maybe you should read about him if you’re looking for that type.

The guy I do want to tell you about is the one who lived five states away. We texted all the time. This created many moral dilemmas, such as, can I text about a blow job while I’m eating McFlurries with my kids. (Answer: Yes)

One night I was at the gym, and I was naked, getting ready to shower, when a woman in my aisle said to me, “Are you Penelope Trunk?”

I knew it was going to be bad. I reached for a towel to cover myself, realized I forgot to bring one, and then said, “Yes.”

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She said, “I love your book so much. I wish I had it here for you to sign. Can you sign a piece of paper?”

Insane request, yes. But it’s hard to think fast when you are naked. So I signed the paper. Then I told the guy I was dating. He said, “The story would be so much better with a photo. Send me one.”

I laughed.

He did not laugh.

I said, “Naked?”

Of course, he said yes.

He said, “Do it now,” like he is a 15 year old fixated on getting his hands on his first piece of porn. Or like he is Mickey Rourke in 9½ Weeks. Not that I saw the movie. But I read the book and the surrounding literary criticism so I could understand the dynamics of men giving orders to women.

Sort of hot. If you let the guy do it.

So I went to the back of the showers, and I laid down in a dressing room because if you lay down you look thin. I clicked. But then my breasts sort of flopped to each side.

I spent an hour taking photos. I moved dressing rooms. I tried standing in the shower without the water on. I remember reading that Ansel Adams took 1,000 shots for each masterpiece we know today. I think I’m the Ansel Adams of nude self-portraits. After 1,000 tries, I had a masterpiece. Perfect lighting so that nothing looked fat, perfect camera angle for smooth skin and fluffy breasts, and perfect timing because he surely thought I would never send the photo, so it was like a surprise in the mail.

Do not tell me that sending naked photos of myself is dangerous. Because sure, he could show it to his friends, but so what? I look great. I hope he can get the photo in Maxim because I might never look that good again in my whole life.

And what will his friends think of me? Probably nothing. Because they have women sending nude photos of themselves. It’s not that big a deal. You know how I know? Because the state of Vermont, (and other states as well) is trying to pass a law that decriminalizes sending nude photos of oneself if you are underage. That’s right: For years, even though kids were sending nude photos of themselves to someone they wanted to show it to, the act was illegal—an act of trafficking in child pornography.

But sending nude photos is so common today that lawmakers are forced to treat it as a mainstream courting ritual and legalize it for all ages.

Sending a naked photo of yourself is an emotionally intimate act because of the implied trust you have in the recipient. When you act in a trusting way—like trusting the recipient of the photo to handle it with care and respect—you benefit because being a generally trusting person is an emotionally sound thing to do; people who are trusting are better judges of character. This is because people who are trusting get burned a lot and learn form that. People who are suspicious all the time won’t learn nearly as quickly who is trustworthy, according to research reported in Psychology Today.

Also, if you’re worried about your career, you can relax. Anthony Weiner, the most comically animated, intellectually captivating, Internet-ready member of Congress, just tweeted an alleged photo of himself in underwear. Or not. Actually, it was not really his whole self, just the what’s-covered-by-underwear self. But his constituents don’t care. Probably because they’ve all sent the same sort of photos.

But here’s some good news: As long as you make yourself look hot in the photo, you’ll probably be okay. Because good-looking people earn more money, have more friends, and have more fun in life than the not-good-looking. So if you can figure out how to take a good photo of yourself, text it to anyone you want. And if you want to know how to send the photo via Twitter, ask Congressman Weiner for some tips.

Penelope Trunk founded three startups, including Brazen Careerist. Her career advice runs in 200 newspapers. Inc. Magazine called her "the world's most influential guidance counselor."