Some things need to be said:

It seems that in the U.S., people give way too much importance to losing their V-card. It's ridiculous.

It's ridiculous partly because most people who laugh at virgins aren't getting laid that much at all. I mean, I'd bet the majority have only been with less than like 15 or 20 partners.

Heck, I'd bet it's even less than that, and the harder the person makes fun of virgins, the lower the number of partners they've had.

There's a kind of empathy one gets after stopping to count, and most people don't have it.

So it's ridiculous to make fun of a virgin, because, well, we all have been virgins at some fucking point in life.

The irony about this is that it becomes really important to the point where it reeks out of every port, and usually, girls don't hook up with guys who are that desperate to get laid. They get laid with guys who are horny, yes, but not desperate.

Someone who gets laid regularly is horny but not desperate. He likes sex and knows he can get it anywhere.

And the problem is that virgins let themselves be judged by people with whom they're only separated by few nights.

Okay, this having been said.. If this guy was trying to abstain, I'd understand. And even then (when you are actively abstaining, it's hard).

What I want to say is this: This guy wouldn't mind sex, so where's the problem?

He's not deformed as to make it hard for him. It's not that looks don't help, but looks amplify one's ability to get laid: They get you on the table, it's up to you to close.

I know several very good looking dudes who struggle to have sex, while we live in a city where it's easier to get laid than to find a public toilet. Girls notice them, they give them the eye, etc, but they're clueless and don't know what to make of it.

Looks amplify ability. If it's 0, it's really hard to get anywhere.

The guy isn't ugly, he can help himself though by getting back to reality:

The last rejection he had was in 1999. That's 15 years ago.. I think it's a lot. Revolutions for Independence lasted less.

One of the main problems guys who struggle with this stuff is that they dwell waaaaaaaaay too much on an experience you shouldn't take that seriously. Many guys take this shit way too seriously. He's interested in a girl, she isn't interested in him. Period. Where's the problem? It's not 100% personal. Just move on. They take it directly to heart and feel it is a deep critique of who they are, of their own person. It's just the way it is, and you mustn't accord any importance to it, unles...:

Most girls aren't interested in you.

This is not normal. If you're average looking, then at least like 50% of girls wouldn't mind getting to know you. If you are hot, this percentage rises. Take a movie star, most girls wouldn't mind getting to know them, and _yet_, you'd find girls who find a popular good looking actor not attractive.

That's the beauty of it. There is enough for all tastes.

From the percentage of people who wouldn't mind getting with you, there's a sub-category of people who would _definitely_ want to be with you.

If _most_ people don't even consider being with him, this would indicate something deeper. But I doubt it is as bad as he describes, because who knows all people to know most people. So most is only as big as how many people you talk with, and for a guy whom the last rejection dates to 1999, I doubt it's a lot of people.

Everybody gets laid, it's the easiest thing and it can make your life miserable if you don't have the discipline to say no, because you wouldn't be able to get anything done. So there's definitely something he's doing wrong.

Also, it's a probability thing: If his day to day life doesn't involve interacting with women, it's going to be hard. It's going to be "something". Like it would be an event to chat up some girl: It shouldn't be. If it's an event, it's stressful. If it's stressful, it's avoided. If it's avoided, it won't happen. If it doesn't happen, he won't get laid. If he doesn't get laid, it becomes hard. If it becomes hard, he gives up. If he gives up, he won't even bother chat with girls.

If the last rejection happened 15 years ago, it's no wonder he hasn't had a girlfriend. It's logic. I mean, he could be the most awesome person on the entire Earth, if he's home, no girl will hear of him. If he's not out there, no girl would be able to see how awesome he is. That's akin to building the greatest product in your basement, and not getting it out there. It's unheard of and people can't benefit from it.

Also, there's the notion that I, as a non U.S. person notice: It seems (from what I saw) that there's this mindset that men think women are "giving them" something when they have sex. This irks me.

Many people fail to really notice what goes on in an interaction. I mean, people interested in start-ups should be getting laid left and right, because they understand concepts like failing early, like iterating, etc..

And they understand concepts like: Minimum Viable Fucking Product.

There's a minimum to have to get laid. Strip it out. Make it happen, add features.

Features definitely help, but if the product "does" the deed, it's a win.

A good question is: If I were a hot girl, would I be interested in me?

This is a really hard question that seems really easy in a Peter Thiel way. Everyone thinks this question is easy, while it's very hard. In a Feynman way, too, as it's really easy to fool ourselves.

You talk to a guy nobody would touch to save the planet, he thinks he's desirable. Is that backed? Nope. 100 girls reject him and he still sees no problem in himself, it's the girls' problem for they're _insert favorite curse here to justify non-existing sex life_.

You gotta be realistic. If you had a sister, who would you want her to be with? I mean, there are some standards for fuck sake.

And I know this post would get down-voted like crazy, because it touches a nerve. But bear in mind that that thing lady-men have, it's due to experience. It's due to failing early and often. It's due to dusting it off and not taking it seriously. It's due to them learning their lessons each time they interact with a girl.

There's the other thing that, well, most dudes are chodes. Like a lot of dudes would get clingy because they're not getting laid enough.

Okay, I'm just rambling and all. Anyway, as a conclusion:

Sex isn't a big deal. It's rather easy when you unclutter the way you look at it, and if you're willing to do the work early on. If you're willing to expand your envelope, fail early and often to see that finally: It's not that bad. Nothing happened when a girl didn't find you attractive.

The first times it happens, it's actually liberating.

And if you are in his situation. If you are a virgin, then don't feel the pressure from someone who'd have gotten laid the same as you in a relatively short period of time. The pressure doesn't exist. It's just mental masturbation from people who've done nothing worthwhile in their life (I mean, gotta be a loser to make a virgin self conscious of not doing something, especially if you struggled with it yourself).

Just be cool with it. Own it. Heck there are some girls who get turned on popping your cherry (there's a reason some dudes pretend they're virgins with some girls, but it takes practice to spot who'd smell blood and go for the kill, and who'd find it weird).

Just chill, it's no big deal. Chat up people, not just girls. Try to take it somewhere. Do something with your life (actually getting shit done, having accomplishments is a major turn on for girls. I don't have that, but people who have their shit together are really attractive). Have something in your life that's way more important than getting laid, and paradoxically, getting laid will be even more easier.

Though it's tricky: Don't feel bitter, or cloak yourself in an attitude of "Pfff, I don't care about sex". Don't lie to your self. Own that shit. It's also attractive to be able to tell someone straight: "I'm a bit intimidated/nervous". I mean, God it just dissipates the thing right away, as if having the balls to admit your "weakness moment" makes it disappear.

Take advantage of physical constraints: On the subway, on the street, in the line. Talk to people. You'd be amazed what would happen. I say good morning and smile to people I cross eyes with, it's great to spread a good vibe. Life is good. You meet different people, etc. Anyone who tells you old ladies aren't fun never lived :P