Dear John: Do I Really Want An ‘Escort’ For My 26th Birthday?


A 26-year-old virgin hiring an escort for his birthday, a boss feeling undermined, and the myth of the perfect male body.


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Dear John,

I’m a 25-year-old guy. I’m a college graduate, gainfully employed, happy life, etc., except for one thing: I am still a virgin, mostly, I would say, because I am extremely, extremely shy. A bunch of my friends have gotten together and decided to solve this problem for my birthday. They pitched in to pay for the services of an escort for me in a couple of weeks. It’s all been set up and arranged, and the woman involved knows what the deal is and has assured them that everything will be fine. As the date approaches, I find myself looking forward to it with great anticipation and also great dread. I can’t wait to have this stigma removed and I am really excited at the prospect of the sex itself, but in the back of my mind, I’d be lying to deny there’s a feeling that this is kind of pathetic and shameful. Part of me – a small part – wants to back out, but I feel like I’d be letting everyone down, if that makes sense. This started as kind of a joke, and I went along with it, but now that it’s real, I have somewhat mixed feelings. I’ll decide I don’t want to, then I imagine what it would be like to have this albatross removed, plus the sheer excitement of it, and I’ll change my mind again. Now, more than anything, I’m confused and tired of thinking about it. Any advice?

Waiting Long Enough

Dear Waiting,

I truly understand how much you don’t want to be a twenty-six-year-old virgin, but you’ll remember the first time you have sex for the rest of your life. Is this really the memory you want to have – a meaningless transaction that seems to be for your friends’ amusement as much as it’s for your enjoyment?

DearJohnImage22Becoming sexually competent is a bit of a process. For most of us, the very first encounter is clumsy and awkward. By the third time, you begin to get the hang of it, but the first time is the one you remember. I think you’d have a better experience, not to mention a better memory to savor, if your first time were with someone you care about and enjoy being with.

I understand your impatience – I really do. I know you won’t agree, but there’s really no stigma in not having had sex yet. It’s one of those things that seem overwhelmingly important to you now, but there will come a day when you wonder why you were so fixated on it.

I don’t think going through with this is wrong as much as it just sounds like a bad idea. And if you do go through with it, definitely use a condom. But really, I think you should tell your friends to forget about it. Your misgivings reveal that this isn’t the way you want this to happen. I would listen to them if I were you.

On a related note, you might explore cognitive therapy to learn strategies for overcoming your shyness. Doing so would not only make it easier to meet women, but it would make other aspects of your life, like interviewing for a job, less of an ordeal as well.

Dear John,

I work for a small business and I work in an office with my direct boss. She is a very nice person whom I like a lot. We have a good working relationship but there is one problem and it has to do with the temperature in our office. Last summer she started to crank the air conditioning in our room and begin to complain about going through menopause. She spoke frequently about hot flashes and how uncomfortable she was. I’m a woman and I know that this is in my future but accommodating her physical comfort is making me cold and miserable. I wear layers to work but I can’t wear mittens! I spoke to her about being cold and she just says dismissive things like, oh you have no idea what these hot flashes are like or lucky you, young and very little body fat. So addressing it did not work and what has transpired since then is pretty ridiculous. She will leave the room and I’ll raise the temperature. She’ll enter the room and lower it again. This winter has been just as brutal. She turns the heat way down and I turn it way up. I don’t want to go to the owner of the company because that would really undermine my day-to-day work relationship with my boss. Do you have any suggestions?

Cold and Unsympathetic

Dear Cold,

This seems like a situation that should be resolvable if you’re both willing to compromise a little. You say addressing it didn’t work, but it sounds like you made an offhand comment or two, she dismissed them, and the thermostat wars began. The two of you have to make a more concerted effort.

The menopause issue is a bit of a red herring. Even if her comfort were not under hormonal attack, you would still have to come to some kind of resolution if you simply had very conflicting ideas of a comfortable temperature.

You say you’re friends, so sit your boss down and tell her you understand how uncomfortable hot flashes must make her, but at the same time, a room temperature in the low 60s makes YOU uncomfortable, so first you should settle on a thermostat setting somewhere between what you both desire.

Is it possible to reposition your office furniture for your mutual comfort? In all but the coldest months, a sunny window is significantly warmer than a spot out of the sun.

Finally, you should acknowledge that in a situation like yours, it’s easier for the person who feels cold to take steps to be more comfortable (putting on a sweater, positioning a small space heater under the desk, etc.) than it is for the warm person. After all, you can only remove so many layers before becoming a distraction to your co-workers.

Dear John,

I’m a student who works hard at my studies. I have an extra-heavy course load, plus I tutor at the university. So when I get home at night I have to do homework, and there is no time or energy for going to the gym.

I get the feeling that girls (and guys) find me repulsive because I don’t go to the gym. I have a nice face and a charming smile, but I still feel they want the jock body the media pushes.

Besides putting all my energy into my degree, I don’t have the motivation to go to the gym. Who will look at me anyways? Am I wrong about the matter, or is society wrong about the “perfect male body”?

I’ll Be At The Library

Dear I.B.A.T.L.,

I don’t think your issue is what other people think of you. I think it’s what you think of yourself.

Do you really believe people find you repulsive just because you don’t go to the gym? I can’t imagine most people feel that way, so I can only conclude that this statement offers a little insight into your own self-assessment.

Yes, of course our society places too much emphasis on ephemeral physical attributes – perhaps it’s their very transience that underlies our near-obsession with them. But I think most people, even as they indulge in the celebration of superficial physical beauty, are aware of the shallowness and silliness of it all.

Look around you – many people fail to uphold the standard you’re referring to; you’re hardly unique or unusual. No one is looking at you with revulsion. I’m sure there are people who would judge someone out of shape as being unworthy of their consideration; these are probably the same people who fail to age with even a modicum of grace. I suggest you take advantage of your university’s student mental health services and start exploring why you have such a negative opinion of yourself and why you assume others do, too.

Having said that, I also think you should revisit your attitude toward exercise, not because you’re insufficiently attractive, but because a higher level of physical fitness will give you the stamina you need to meet the formidable mental challenges you’ve undertaken. You’ll make up he time you devote to getting in shape by having more energy and a greater ability to focus on the task at hand. If you’re too exhausted at the end of the day, which is perfectly understandable, exercise first thing in the morning. I’m sure your school has a wide variety of fitness activities, so try different things until you find one you like. Getting in shape needn’t involve dragging yourself to a boring gym, and you’ll be far more likely to stick with something you truly like. I strongly recommend that you consider it, not so you’ll look better (although you will) but because you’ll feel better, mentally and physically.

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Photo credit: Flickr / Flavia_FF


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About John Simpson,

John is a middle-aged family man from Providence. If you learn from your mistakes, he’s brilliant. His column runs regularly on


  1. The sex worker can help a lot if you are open to it and want to. You don’t HAVE to have sex with her nor should it be shameful. It’s probably more nerve racking being with someone you really like and don’t wanna mess it up with vs being with a sex worker who is most likely an expert on how to help shy people.

  2. “The sex worker can help a lot if you are open to it and want to.”

    True but he appears to be a lot like me. I had the same problem … I was a virgin at his age and wanted to lose it. I did lose it to a prostitute. At the time I remember thinking: there is no reason to keep myself pure anymore because no woman wants me so who am I keeping myself pure for?

    This only did one thing for me. It demystified sex and women. I realized that it just wasn’t that great, all this stuff I had been worrying about. I stopped caring about getting a girlfriend after that and just enjoyed my life. I am not sure if this was due to the prostitute. I think it was more due to the fact that I went back to school to pursue a more lucrative profession and I put my energies into that. At school I ended up getting a girlfriend.

    However I often wish I never went to a prostitute. I have never enjoyed it. And I believe in complete honesty in a relationship so I always eventually tell my girlfriends. I haven’t gotten any bad reactions so far but its a thing I always need to worry about in the beginning. And there is an extremely heavy stigma against it in our society.

    So I guess I would say to you just don’t do it. The experience will be a lot worse than you think. You almost certainly will not enjoy it. I am telling you this in advance. Be strong. I know that’s difficult. But right now you are only doing this because you don’t know what else to do. And the stigma of being a virgin is not so bad as the stigma of going to a prostitute. The essential truth is that for a lot of men prostitutes and sex workers simply are NOT worth it. Masturbation is your friend. The small part that thinks this is pathetic and shameful…well its totally correct.

    If I were you I would go to some dance classes offered by a university. You can meet plenty of women there and a lot of them want to hook up. Plus they are often really nice and pretty. Your problem is probably that you aren’t meeting enough women and you don’t know how to ask them out. It will be rough going at first but its your only way forward.

  3. @ Waiting Long Enough-
    The first time really isn’t the big deal that the prudes would like you to believe…
    It’s some kind of hold over from a pre- birth control world…
    Chances are you’ll F like a rookie. Who pars the golf course on their first round?
    Do really remember your 1st time up at bat? Did you clear the fences?
    Hiring a whore is no different than attending ski school or hiring a fishing guide…
    @assman the only person who knows who I lost my cherry with is the one with whom I lost it..
    (At 1/2 of Waiting’s age- but it was the age of Aquarius)
    Honesty and TMI aren’t enemies.


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