This is something I've thought about a lot in recent months, especially as I had an episode of depression related to the fear of being virgin-shamed by future dates.

This is something that isn't a gendered issue (both sexes do it and to each other), but the dynamics are different if it's a man vs. if it's a woman.

One of the things I've often seen from both men and women who are virgins after a certain "cutoff" age (usually somewhere in the 20s) is a deep sense of shame and embarrassment in being a virgin.

I have not been immune to this - at 22 going on 23 (and probably won't be sexually active for another few years at least) I went through a few months of deep depression and regret because I didn't make active efforts to "lose it" in my college years (I was too focused on schoolwork and research and trying to get into med school...I ended up getting in but losing that opportunity due to said depression). I'm a guy, and it's mostly because I was apathetic and didn't feel like asking anyone out (I've dated before but it was during high school). It's true that I may have had hangups about sex, am introverted, and have some degree of social anxiety, which does contribute to the problem.

Since I want to pursue those relationships again in the future, I told some female friends about my situation. They warned me that there are a not-insubstantial number of women who virgin-shame (or "relationship-virgin shame" i.e. shame those who have never had a relationship, regardless of sexual history) and run away from guys past a certain age (sometimes 25, sometimes 30, usually around there) and that it's horrible that it happens, but a male virgin past a certain age is seen by them as a liability because they don't want to be a teacher when it comes to sex, insist on men taking the lead, get clingy, has issues, or get really insecure about it. It's the perception that something is wrong with this person that they haven't managed to persuade any other woman to sleep with them - and they should stay the hell away. That in addition to my already scant dating resume and my "stereotypical virgin" qualities (lack of social graces, video gamer, STEM nerd, awkward) made me panic and get depressed. That was when I started to feel the "ticking clock" - that if I don't hurry up and "lose it", then my dating pool starts shrinking and shrinking to the point where even the opportunity is denied me. I'm aware that those raised in more conventional environments (I went to a geeky/nerdy HS with a lot of kids from more traditional immigrant families) felt the ticking clock much earlier, maybe in high school. So I wasn't directly virgin-shamed, but rather was told that a large portion of my dating pool would.

So basically, the virgin-shaming I was worried about is not from other guys, but from women. Conversely, women are often virgin-shamed by guys they want to date as well, and it's horrible in both ways, but it is in this aspect where I think women have it somewhat easier because the assumption is more she chose not to (frigid, prudish) as opposed to she couldn't.

But, what I want to question is why? Why are so many people making assumptions about virgins, either male or female? Why are male virgins after a certain age seen as losers, creepy, weird, misogynistic, hateful, bitter, ugly, unsuccessful in life (basement-dweller), desperate, potential mass shooter (think Elliot Rodger), and unable to attract a partner, while female virgins after a certain age are seen as stuck-up, unattractive, nasty, prudish, misandrist, cold, overly picky, etc.? Worst of all, this shaming makes it harder for people in that situation to find suitable partners, both due to stigmas held by their preferred gender and because of the depression/insecurities that it induces in people.

Is it because of the media and movies ("40-Year-Old Virgin", "Clueless")? Just a general sense of shock and weirdness? Or is virginity actually correlated with "negative" traits in people, such as haughtiness, sexism, and lack of career success?

This has been nagging at me because I know that this kind of background shaming causes massive amounts of depression among people in that situation (if you see Reddit's ForeverAlone subreddit...holy cow), frustration, bitterness, and people even commit suicide over it - why people think that it's a red flag or the mark of a defective individual at any age or for whatever reason is beyond me.