How to decide whether to hire a prostitute to get some sexual experience late in life?

Why does he have to tell anyone?

Edit: Shit the guy is 40. Finally, he has the sense to go to a prostitute and find out what he’s been missing for 25 years – then go have a blast. Hire two or three, go to a nice hotel – make it an all nighter. If there isn’t anything frighteningly wrong with him (other than his being a virgin) then perhaps this will “shake him up” and be just the trigger for the confidence to meet a woman. God knows it’s about time.

Besides, and I don’t want to sound harsh or too chauvenistic, but blind dates and internet dating and all that – it aint cheap – and most of the time, you know in advance if it includes sex or not. The stigma of a prostitute is just that. I am completely against the sex industry, but it’s a fact and here to stay. Don’t make such a big deal about it. Be like your army – don’t ask don’t tell.

Honestly, it doesn’t matter. Being a virgin doesn’t make your friend any less of a person, or any less of a man.
Atleast he’s not a ravaging man whore like many guys I know.

@Zen_Again He believes that if he becomes close to someone he would feel bad about hiding such an important fact about who he is.

I agree with Zen, why does he have to tell anyone? He should do what he wants to do now and not worry about what will happen in the future. Heck, who know there may not be anyone in the future.

It’s the only way he’s ever going to bang a 20-year-old, which is what you told us he wants to do.

@pdworkin Not the only way but the most likely way perhaps, yes. It’s still possible he could bang one of his students after they are no longer in one of his classes.

@pdworkin

A 20 year old hooker probably isn’t going to be hugely attractive by nature of profession!

I’d stick with not hooker.

If he’s that desperate, there are places that will, for the same money, teach him how to get a legitimate shag.

This was a hilarious film.But if you think it will help,then by all means.just use protection.

@EdMayhew Teach him? Are you serious?

As I said in the previous discussion, I doubt that hiring a prostitute would help a man learn about pleasing a woman. However, if said 40 year old virgin is hung up about his virginity and needs to lose it, he should do it. If he wants to tell later or not, that’s up to him. Personally, I would rather teach a virginal man I loved how to please me than know he’d lost his “cherry” to a pro.

It would be harder to explain a hooker as your only sexual experience than not having had sex.

Unless he’s got stacks of cash laying around, I’d pass. Most prostitutes are absolutely gross, trashy, and disgusting, plus full of diseases. Unless he can get one of those high class prostitutes, I’d urge him to just keep on waiting.

Besides, why can’t he just get a women the old fashioned way? Take him to a bar or something, sheesh.

@squig

Yes, why?

@Zen_Again I read your updated answer and agree with all of what you said, especially: “Be like your army – don’t ask don’t tell.” Unfortunately my friend is concerned that this could impact a relationship (if he ever actualy has one).

@EdMayhew I have a hard time imagining what they could teach a 40 year old virgin that would be of much use to him at this stage of his life. Dating lessons would seem more appropriate for a younger person.

@PandoraBoxx Both would seem difficult to explain. I think most women would have serious reservations about dating someone who was in either of those categories.

I agree that he shouldn’t have to tell this hypothetical person he goes on to date. If he’s acting funny because he doesn’t know what he’s doing, he can simply say “it has been a while.” The woman is more likely to think that he just has strange sex habits than to automatically jump to the conclusion that he’s a virgin.
Just teach him how to put on a condom before this happens.

If he’s 40, and hasn’t had an intimate relationship, then there is something that he’s doing wrong, and he’s doing it wrong over and over again, without realizing what it is.

From this female’s perspective, I would respect the person more for being a virgin. Actually, I think it’s kind of sexy.

@Parrappa He can affford to get a high class prostitute, yes. After 20 years of not dating, he’s got plenty saved up for a rainy day.

@squig

If he’s still a virgin at 40 I’d imagine there’s quite a lot they could teach him! :)

@PandoraBoxx That thing he’s doing wrong is: not dating! As @pdworkin remembers, he likes 20-somethings (he’s a college professor and is attracted to women like his female students). But because of rules about dating students, he has not been able to get into a situation that has been easy for him to date an ex-student.

He hasn’t dated in 20 years? So the problem is really not that he’s a virgin, but that he doesn’t know how to have any sort of relationship with women. Dating 20 year olds won’t help that.

He needs dating lessons.

Honestly he should watch “The 40-Year-Old Virgin” and take notes. It is a comedy, yes, but it is very telling:)

@PandoraBoxx What type of lessons would those be? I have a hard time picturing how information that is intuitive like this could be passed on without actually putting in the time to get real world experience.

Virgins don’t bother me, shit we’re all virgins at some point. And we all lose our virginity at different times. So his is longer than average. What the fuck ever, buy a Fleshlight and deal . Or, go to The Bunny Ranch. Some people are gonna find the hooker experience a turn off, some people won’t – the same goes for virginity.

He shouldn’t be making this decision based on a hypothetical woman in the future’s possible opinions on that matter.

He should absolutely be making this decision based on how he feels personally about either outcome.

And none of us can help him there, this entire thread is kind of useless because of that.

Dating lessons, seriously. @PandoraBoxx has got the idea.

If you’re gonna do it, do it right.

Has this man been in a cave? where has he been for the last 40 years? can you teach an old dog new tricks? maybe not in this case. this is amazing.

Go on a dating site, connect with people stating up front that he doesn’t have much experience dating, and would like to meet women to take out and spend time with. You cannot go to a prostitute and expect it to cure social ineptitudes.

Hell, date older women for awhile to get over problems dating. There is a shortage of decent, available men between 50 and 40. If he’s interesting and not a jerk, he shouldn’t have a problem with dating or sex. Once he gets over that, he can engage in thinking he’s God’s gift to 20 year olds.

@EdMayhew At the risk of repeating myself, what do they teach in these lessons?

To be fair though, and to nudge him in a practical direction -

Very few woman find warts, HIV, herpes and syphilis more attractive than virginity. In fact, I’d say no woman prefers those.

@asmonet It’s possible to avoid those problems if you’re careful. I know this for a fact.

@john65pennington: Not everyone is the same, I knew a woman who had never kissed her husband of thirty years. Not even on their wedding day. And it wasn’t a marriage of convenience. They just didn’t.

@squig: Anyone who took Health in high school knows about condoms, good for you. My point is, shit happens.

@PandoraBoxx “You cannot go to a prostitute and expect it to cure social ineptitudes.”

Quite true.

In a society where dating usually begins at age 14 or so, what happened to keep this man from ever having dated? Don’t you agree that he could use some psychotherapeutic assistance to deal with the underlying reasons for his avoidance patterns? (And believe me, being attracted solely to 20-year-old girls is avoidant behavior, too.)

@asmonet Absolutely. There’s a risk involved and he has to weigh that risk against any potential benefits.

Hey, here’s a thought. Why don’t you stop concerning yourself with your friend’s sex life and start worrying about your own?

No one would judge him because he went to a hooker.

@holden shhh. he is.

@holden Just want to help my friend. Is that so wrong?

It is far easier for a forty-year-old to bang a twenty-year-old then it is for a twenty-year-old to bang that same girl.

@Kelly_Obrien How does that relate?

@pjanaway: Wrong.

@squig It’s the only way he’s ever going to bang a 20-year-old, which is what you told us he wants to do. See @pdworkin statement to see how this relates.

@asmonet – Well if you judge someone for doing it then you should be killed. Nuff said. lol

If he is a close friend, tell him that it’s never too late to start, and if he finds a serious relationship where he wants to be intimate, the other half in that relationship will not judge him for being a virgin.

Also tell him that by going to a hooker he’s treating the symptoms not the problem.

@pdworkin I think he’s fucked up, yes.

Sure, get yourself a prostitute. Wear condom(s). Then don’t tell anyone about it later.

@pjanaway: I never said I did personally, people have different standards and moralities. And everyone judges people on occasion, even you. Guess someone should kill you as well. Have fun with that attitude of yours.

If your friend chooses to hire a prostitute, watch out for the cops.

@azlotto There are legal places to do it. It won’t be an issue.

Ask your little friend. But seriously, it is legal in Nevada, and I don’t think it’s anything to be ashamed of. But I certainly would take every precaution.

I don’t think it’s unusual to not start dating at 14. When you’re young it all depends on how you get on with the dateable people around you. I started “dating” at 17, one of my best friends is a total catch (she’s cute, smart, funny, nice, everything a guy would want) but went to a high school where she wasn’t interested in the guys and the guys weren’t interested in her (the only artsy and politically active teen in miles).

She’s not confident as a result, since she didn’t get any practice as a teen, and now just does not know how to talk to guys.

The moral of the story is that it’s not unusual to miss out on the key dating experience years, but he has to be confident and try to figure out how to do it anyway. Going to a prostitute is not going to help that.

“Fucked up” isn’t a useful way to describe someone who could use some counseling. The best thing you could do for this man would be to encourage him to get some assistance, so that he can spend the rest of his life more happily.

@sliceswiththings I agree. It’s possible, if anything, it may make everything worse.

@asmonet – Who said I was talking about you.. lol

Anyway I’m right, you shouldn’t judge people, if they want to go to a hooker then let them, its no one elses business. You can’t base an opinion on someone just because they went to one in previous years.

@pdworkin I think he’s going to get some counseling but is not convinced a counselor would accept his premise – that he wants to date a 20-something year old woman OR no one at all! He sees only one alternative to dating a 20-something year old woman and that is hiring prostitutes. Most counselors, it would seem to me, would not accept this logic.

No good counselor is judgmental about these things. If he finds a judgmental counselor he should leave and find someone more professional.

@pdworkin Fair enough. That’s reasonable.

@squig… Expensive date to fly/drive to a place to hire a prostitute legally.

Wait he wants to date a twenty-something or no one at all? In that case “date” is the wrong word. For many men at that age, dating leads to marriage and kids. A twenty-year-old is probably not looking for marriage and kids with a forty-year-old. If he has no intention of ever dating with the purpose of settling down, it sounds to me like he just wants to screw a hot young thang. In that case he wouldn’t need “relationship experience” and could just go to a hooker.
As a 21-year-old, the only time I would actually date a 40-year-old is if he saw me for the woman that I am, regardless of age, and he would still want to date me if I was also forty. If it’s just the age he’s after, that’s a dealbreaker, sorry.

@azlotto Money is not an issue here.

@sliceswiththings ”If he has no intention of ever dating with the purpose of settling down, it sounds to me like he just wants to screw a hot young thang.”

He wants both and does want to settle down with his 20-something bride.

@pjanaway: Who you were intending to insult was not as clear as you might have hoped, regardless I covered any response for myself or if you were referring to people everywhere. And I still thinks it makes you look terrible.

You’re judging people for judging people. Sound a bit retarded to you?

@squig Fair enough. I guess I misinterpreted it.

@sliceswiththings “As a 21-year-old, the only time I would actually date a 40-year-old is if he saw me for the woman that I am, regardless of age, and he would still want to date me if I was also forty.”

That’s something you would never know and none of us ever knows – the “real” reason why someone is with us. If you were 21 and fell in love with a 40 year old, you would have believed it had nothing to do with your age. We all believe what we want to believe. It’s what keeps us going.

@squig exactly. So keep believing that all your sexual and social inhibitions will be cured once you score with a prostitute, ‘cause, apparently, you’re going to base your beliefs on your own desires with or without our commentary.

Ok, so what happens when he turns 50 and she is consequently no longer 20?

I’m sorry but if this guy doesn’t want people to judge him when he himself is so narrow minded then he doesn’t deserve to get laid, and that’s probably why he hasn’t – he sounds like a creep to be honest.

If he just had confidence issues or whatever that would be fine with me, but it looks like it’s pretty much self inflicted. For that reason get a hooker, at least that’ll keep him the fuck away from all the innocent young girls out there.

xx

Sorry.

Ok, so what happens when he turns 50 and she is consequently no longer 20?
I’m sorry but if this guy doesn’t want people to judge him when he himself is so narrow minded then he doesn’t deserve to get laid, and that’s probably why he hasn’t – he sounds like a creep to be honest.
If he just had confidence issues or whatever that would be fine with me, but it looks like it’s pretty much self inflicted. For that reason get a hooker, at least that’ll keep him the fiddlesticks away from all the innocent young girls out there.
xx

@EdMayhew I think this kind of avoidance is evidence of a psychological problem which can be productively dealt with in therapy. This man can’t help how he is feeling today, so maybe he shouldn’t be so harshly criticized (and I have criticized him quite harshly myself, so nothing personal) maybe it would be best if he were encouraged to seek assistance.

@pdworkin I already did the encouraging to seek assistance, and in a less ‘you need a shrink’ kind of way, however it bothers me a little when people ask a question if they seem already to know the answer.

A la @holden “apparently, you’re going to base your beliefs on your own desires with or without our commentary.”

Having sex is not rocket science. But if he feels that he needs experience having sex before he goes into a serious relationship then he should go ahead and do it. I would think that the person who does go into a relationship with him would want to go into a relationship because she likes him as a person, not because she wants a sex god. Anyhow, I think he should just do whatever he considers best. I wouldn’t judge him either way.

Being that my boyfriend is around your friend’s age, I would have been upset if I found out he slept with a prostitute. That doesn’t say much about his character. If he was a virgin, that wouldn’t be so bad. I could understand someone being a virgin but I can’t understand someone hiring a prostitute. I think your friend needs to think this one over a lot more before he decides. Also, he would have to tell his future girlfriend about the prostitute. That’s just not something that you keep to yourself. Your friend seems like an honest guy and this doesn’t seem like something he would do or would want to do

What do you jellies think about Surrogates?

So let’s suppose he goes to the prostitute, gets his fantasies fulfilled. Then he finds a hot coed who is willing to go out with him and not turn him into the university board of trustees for intellectual seduction, sexual harassment, or sexual coercion. She’s finding him to be attractive and is flattered by the attention. She tells him about her exploits with the Lambda Chi house, and he says,....what? The truth that he’s only been with a prostitute? He lies and makes up a fake relationship, when he knows nothing about relationships? He says nothing, and moves on to another 20 year old, hoping to perpetually avoid the issue?

Okay, I had not read all of the responses but now that I have I must say this. If he couldn’t get laid by a 20 something year old when he was around that age what makes him think that he can now that he is 40? I guess he is going to have to hire a prostitute.

@PandoraBoxx @squig Social ineptitude is not always cureable. Does this gentleman have some condition, such as an autism-spectrum disorder or some kind of social phobia? Visiting a prostitute will not help him there.

I agree that it’s not always curable, and it’s definitely not curable if you have an unrealistic fantasy playing in your head. I do know several women my age (50s) whose second husbands are of the socially awkward types, and they are quite happily married; they adore and appreciate their husbands. They’re hard to meet.

I think you may be limiting yourself with choices of life partners. Would your “friend” potentially be on the same maturity level and have a similar lifestyle to a 20 year old?

There may be 30 and 40 year old woman who may be just as suiting for a relationship, I personally wouldn’t cut off my options.

My apology for not answering the question directly, but…

…why does anyone have to know but him?

His mistake is choosing not to date rather than date anyone over 30. Even if he doesn’t want to marry them, he can he go out and have a nice time with a woman who is out of her twenties? Most people don’t marry the first person they go out with.

He needs experience with dating, conversing and having a relationship with a woman more than he needs to have sex.

He needs to go to the Bunny Ranch and get this “virginity stigma” out of the way.

@EdMayhew “Ok, so what happens when he turns 50 and she is consequently no longer 20?”

Good question.

There are two scenarios I can think of that seem within the realm of possibility but since this guy is basically an unknown entity with respect to relationships, it’s hard to have any certainty about which one is more likely.

Number 1: After spending 10 years with a woman he is attracted to, he is a changed man and becomes a devoted husband, forgetting about his prior interest in 20-year-olds and is completely satisfied with his now 30-year old wife or girlfriend.

Number 2: After spending 10 years with a woman he was once attracted to, he discovers that his attraction has faded and he either ends the relationship to pursue another 20-year-old or he cheats on his girlfriend or wife with a 20-year-old student or he cheats on his girlfriend or wife by hiring a 20-year-old prostitute.

@kheredia “Having sex is not rocket science. ”

Easy for some to say perhaps.

“I would think that the person who does go into a relationship with him would want to go into a relationship because she likes him as a person, not because she wants a sex god.”

There’s a big difference between being a sex god and having no experience whatsoever at 40 years of age. That would be a turn-off for many people.

@squig

So basically he’s not got a plan, other than the girl has to be 20. IMOH, he sounds like a really boring guy but whatever. OO, is that the sound of someone posting a question that is worth my two cents? Sorry, must go, better things to do.

xx

@Justnice “Also, he would have to tell his future girlfriend about the prostitute. That’s just not something that you keep to yourself. Your friend seems like an honest guy and this doesn’t seem like something he would do or would want to do”

He definitely does not want to be in this situation where he feels he has to lie about something that is so central to who he is. He’s quite a sincere guy and has a lot of good relationships with men and women from all walks of life. Very few people have even guessed the truth of his situation. But the dilemma you have pointed out is one of the big issues he is facing. He feels he needs to get some sexual experience so he is not a complete novice but he is also concerned that revealing that fact to a future partner could cause that person to walk away. Actually I suspect it’s more than a fear of someone walking away. I think he has a certain image of himself that he wants to project to his future partner and he does not want this fact about him to alter and tarnish that image.

@PandoraBoxx “So let’s suppose he goes to the prostitute, gets his fantasies fulfilled. Then he finds a hot coed who is willing to go out with him. She tells him about her exploits with the Lambda Chi house, and he says,....what? The truth that he’s only been with a prostitute? He lies and makes up a fake relationship, when he knows nothing about relationships? He says nothing, and moves on to another 20 year old, hoping to perpetually avoid the issue?”

Yes, there is almost certainly some dishonesty called for in such a scenario. The question is whether it’s a level of dishonesty that he can live with without it interfering with any potential relationship.

The only way to avoid this dishonesty would be to forget about the prostitute idea and tell someone up front that he’s a virgin and try to work through it with that person if she gives him a chance.

“I agree that it’s not always curable, and it’s definitely not curable if you have an unrealistic fantasy playing in your head. I do know several women my age (50s) whose second husbands are of the socially awkward types, and they are quite happily married; they adore and appreciate their husbands. They’re hard to meet.”

There is definitely a fantasy playing here but it’s not entirely unrealistic since he has come close to having relationships with former students. That potential has held him back from “settling for” relationships with older women.

All of your answers were very insightful – thanks.

@kheredia “If he couldn’t get laid by a 20 something year old when he was around that age what makes him think that he can now that he is 40?”

He is a college professor and has a level of respect and, well, power that he did not have as a 20 year old. That has made him more attractive to 20 something year olds by all accounts. Whether you think this is morally bad, it has been made clear to him that this is the case.

@stranger_in_a_strange_land “Social ineptitude is not always cureable. Does this gentleman have some condition, such as an autism-spectrum disorder or some kind of social phobia?”

He might be a goddamn idiot but he’s not autistic. It’s much simpler than that.

@Rachienz “I think you may be limiting yourself with choices of life partners. Would your “friend” potentially be on the same maturity level and have a similar lifestyle to a 20 year old?”

There’s no doubt that he is limiting himself in his choice of life partners. He is consciously and deliberately doing so. As for the maturity issue, that’s hard to say. In some ways he’s more mature than a 20 year old but in many ways just as immature. But I think there are 20 year olds that he could be quite compatible with in a relationship.

“There may be 30 and 40 year old woman who may be just as suiting for a relationship, I personally wouldn’t cut off my options.”

Neither would I. Removing options is never the “smart” thing to do. But this is the nature of his desire and he does not feel there is anything he can do to change it.

The question is what the best next step is for him – hire a 20 year old prostitute to get some sexual experience or go into his next relationship a virgin and admit that up front.

What do you think would be more appealing to a potential partner?

@SABOTEUR He thinks that hiring a prostitute is an important enough fact that he owes it to a potential partner to reveal this information to them and he is concerned about the potential consequences of that revelation.

I think you are seeking support for decisions you have already made. You have an answer for every objection, and it does not look like you are serious about seeking counseling. I would say you will just have to be disappointed for a few more years, and maybe one day you will be moved to decide to live, instead of to play a theater part.

@Supacase “His mistake is choosing not to date rather than date anyone over 30. Even if he doesn’t want to marry them, he can he go out and have a nice time with a woman who is out of her twenties? Most people don’t marry the first person they go out with.”

Agreed. This approach makes sense. Unfortunately, he has a very clear idea of what is and is not attractive to him and dating women closer to his age does not fit into that picture. He is a very stubborn person.

“He needs experience with dating, conversing and having a relationship with a woman more than he needs to have sex.”

I completely agree with this point. Not doing so is perhaps the biggest mistake he has made.

@pdworkin “I would say you will just have to be disappointed for a few more years, and maybe one day you will be moved to decide to live, instead of to play a theater part.”

Well put and I would say so too. Quite seriously.

There is no lack of good sources of information on all the how-to’s of sexual relations. Learn to develop an honest and truly intimate with members of the gender to which you are attracted. I guarantee you that in a genuinely intimate, loving relationship, the physical stuff will take care of itself even without prior practice.

A hooker can not prepare you for the kind of relatiionship you want and deserve.
Lawrence PhD (Psych)

I would say… get a room for the weekend in las vegas… and get TWO girls with plenty of energy drinks! We are talking about straight humping… not social etiquette!

—-editing

@squig I don’t see what the problem is, then. If he’s that concerned about what his potential partner will think, then he shouldn’t hire a prostitute.

And if he’s that concerned about what his potential partner thinks about him being a virgin, then maybe he should de-virginize.

The thing is, he can’t have it both ways. He’s gotta He has to man up and make a decision. Once that decision is made, he has to own it.

He can’t go through life indecisive because he’s worried about what someone else might think.

There is a third option, though.

He could stop worrying about this altogether,
accept the man that he is, and
let the chips fall where they may.

@all Thanks for all of the responses. Looking back over this thread, there is a lot of great feedback here, covering many different angles on this issue. This has been very helpful.

Your friend needs to do worry about how he feels about those choices. If he spends his life worrying about how others are going to judge him, he is going to miss out on a sh*t load of living. The most important thing this man could do for himself is make a decision, all by himself, all for himself, especially in this arena.

How much money does he have?

A holiday to China will cure him. I guarantee it ;) And he won’t have to worry about finding the 20 year olds as they’ll be throwing themselves at him – an older laowai is very very attractive to the young ones. And hell, you gotta love their cute bodies, shiny black hair and exotic eyes ;)

Or a fun trip to Pattaya could be just as effective. Just watch out for the ladyboys…

OK I know I’m going to get flamed for this response…of course I don’t condone the older foreigner with young Chinese girl combination. I loathe it. My partner and I are both in our mid 20’s and we will be marrying (yes, she’s Chinese). But I see so many foreigner ‘players’ running around here.