It's pretty simple. Prior to her rule, she just never met anypony she liked. Post rule, she took her time to get in the swing of things. Fighting Sombra and Luna made her need to take more time. The time she took lasted 250 years. By this point, she is seen as a virgin Goddess, utterly unapproachable. By the time she raises a pony to a similar status, she would kind of like love of the romantic nature, but Cadance only likes stallions in this headcanon.

Her best chance is Twilight's ascent.

5384144 Or you can do nearly a virgin Celestia, in which it's been over a few thousand years since she last took a lover. Alternatively, you can do "Ugh, I don't want to be worshiped, and the few I take a shine to are intimidated by having a lover who will never age. I don't need any of this."

I misread that last line as "Her best chance is Twilight's accent."

Now I'm thinking about how that fic would play out.

There's lots of ways of playing her as a virgin.

One is that she's asexual.

Another is that she's just not been interested in anyone - it is hard to pique her interest, and no one has.

A third is that when she was younger, she kept putting off finding someone )or, alternatively, was gay and it wasn't accepted back then), and then when she finally got around to it (or being gay became accepted), everyone in Equestria felt like a kid to her. They're all her little ponies - how could she romance one?

The inverse there is also possible - that she's an untouchable goddess in the eyes of far too many ponies.

Or possibly, everypony looks up to Celestia too much - Celestia feels like she can't pursue anyone because her advances would freak them out or they would feel pressured to consent regardless of their personal feelings. This could be built into a personal tragedy and could form some core of conflict - either they have to overcome Celestia's concerns about a relationship and their ability to say no, or, alternatively, Celestia ends up making a pass on someone, they are nervous about it or seem to consent out of a sense of obligation, Celestia backs off, and then the person either has to figure out that they do actually like Celestia (and then overcome Celestia's new reluctance about it after their initial reaction) or they realize that they hurt Celestia and have a heart to heart about it.

Another is that she's simply been too busy for a relationship, but in reality, it is not really her being busy, but her simply not bothering to make the time for it. This possibility comes with a nice built-in conflict - someone seeking a relationship with Celestia has to make her make time for them, and/or loop the other princesses in on it. Or possibly, Celestia herself realizing she's built herself into a cage, and not really knowing how to change her ways.

Or it could be that she's worried that if she falls in love and her lover dies, she'll be crushed, and so she has kept herself apart because taking a mortal lover seems depressing.

Or it could be that she has a feeling of noblesse oblige and feels like having a relationship and starting a family of her own would detract from her rule of Equestria.

Or maybe she just figures her hoof is enough, and is kind of scared of having a real relationship with somepony, because she has few enough friends and doesn't want to screw it up. Possibly justified by her having screwed it up before and being left feeling lonely.

5384282

Or possibly, everypony looks up to Celestia too much

This forms the basis of a lot of conflict in Celestia shipping, not just a backstory reason for her virginity. I think it also works better when combined with other reasons, like not bothering or getting too involved in ruling the country. It becomes the catalyst upon which all other conflict is built. Like, she doesn't bother to try, and when something does come along by some coincidence, it fails because she has the niggling little thoughts of "It's only because they practically worship me as being perfect, etc. etc."

5384144
I have to ask: Why?

What point and purpose is served by having Celestia be a virgin? How does it influence or become the conflict of a story? What difference would it make if it has been generations since her last lover? Is virginity a shorthand for some other virtuous concept? Could that concept be expressed by other means?

5384144 I honestly do not like the concept of "virgin Celestia". But I don't like the concept of "virginity" in general. Sex is a natural and important part in the lives of non-asexuals andthe idea of never expressing it is kinda like saying that you never ever go to the bathroom or blow your nose. Heck, the complete absence of sexual stimuli in the average person (again, asexuals excluded) can lead to severe mental problems. I always assumed that Celestia was smart enough to take good care of herself in every way possible, if only to be a competent and collected ruler at all times.

5384144

How to do Virgin Celestia right

With your penis.

5385115
That is a remarkably unhelpful answer, especially in the context of this group.

5384367
5384379

You raise good points, but I assume ultimately it's down to the author's preference whether she is or not. I can't speak for others, but I take somewhat of a shine to the idea purely in the context of 'true love' stories, especially for Twilestia. The lack of sexual experience is but an extension of the lack of relationship experience. The first love is always the most intense, and the idea that their first love is one so powerful and passionate that it can last untold millennia is, to me at least, an appealing concept.

My two cents at least. Again, all up to preference.

5385559
Which is fine. I guess my whole thing with the "why?" is meant to be more of a "does this make sense for the story?" kind of question. I'm not saying Celestia can't or shouldn't be a virgin. I'm just saying that making that decision should be considered in the context of what will come across and what it means in the larger context of the story and the characters.

5385647
A perfectly valid point.

5385559
Not quite sure how a constructive comment reflecting on my own opinion that in no way impinges on anyone else's earns a downvote, but hey, internet.

Relevant Headcanons:

Celestia is Demisexual. Virgin Celestia has done everything in the book except have sex with somepony.

5384379
People go without sexual stimulus all the time and the idea that it leads to mental illness is pure and utter bullshit used by certain people to justify their promiscuity. People have done so on a regular basis with zero ill effect. And indeed, it is hardly surprising; there's nothing biologically essential to sex and having or lacking a sex drive makes pretty much no difference.

There's nothing wrong with people valuing virginity. It is their own choice.

Whether or not someone is a virgin in a story should be based on the needs of the story, as noted by 5385647

5385959 There is a difference between lacking a sex drive and having no sex, which is perfectly healthy. Or having a sex drive and suppressing it constantly for no good reason. And saying that there is nothing essential to sex is... sorry, but sure, you can survive on unspiced rice, vitamin pills and water. But sometimes you WANT a cake and some coffee. Same with sex: It sets free tons of neuro transmitters that make you happy, it relaxes and it has several medically proven positive effects on the body.
Look, I am demi-sexual and I am about as promiscous as a male bee (there is one queen in my life and I am probably not gonna be the one who gets to do her) but I am not gonna argue with the people who teach that stuff in psychology class and write papers on sexual therapy.

Maybe it is just me, but virginity is basically on the bottom of the "important traits" list (unlike kindness, generosity, loyalty aso), so I don't see the appeal.

5385959
5386171
To Davesknd's point, making a character a virgin is a choice that should be given some strong consideration. There are other ways of bringing across the "desired" traits without resorting to the problematic shorthand of virginity. Ultimately, sex or the lack thereof is a big can of worms. Treating your characters with respect becomes even more important when you're talking about this, because the audience is going to be trying to identify with them. If it's handled poorly, you just alienated them.

And I would argue against valuing virginity. It's neither good or bad, in and of itself. It's the traits, thoughts, and actions that surround it that matter.

We're going to leave it at that, because this is going down a road that risks a discussion that won't end well

5386327 You are amazing, completely right and I want to cuddle you... which you might not like since you enjoy harder stuff, so... though luck

5386629
I like cuddles too. After care is just as important

5384144 i say her momma was mean and put Celestia in a chastity belt and then her mom died and well belt is still on, she cant get off because it curse....i mean bless that only her one true love will be able to get it off. so for last oh say her whole life she has not be able to get it off.... Luna was same but meet her true love at young age.....

5386667 That's an interesting if gimmicky idea. We'll say that it's because Celestia's mother had been hurt before in romance. Let's also say it's spell based and invisible most of the time. We'll say that every pony gets one, and nearly all ponies meet their true love in their lifetime. We'll also say it works again after widowing, because why should a person have *one* true love. You can turn it off to, umm, do your business and stuff. What do you think?

5386943 good idea but I was think Celestia's mom is a little old fashion in thinking her daughter should save them self the wedding night with they one true love. but your idea work as well. I just think now how luna found her early in life, got marry love died she do what ever and offend tease Celestia about it, then go to cannon, she ruler people think she a virgin goddess but don't knew about the chasity belt, she use magic to hide it, cause of her duty and such she never had time to find true love but when she meet a young filly she feel something but the true love thing has to go both ways... she force to choose to guide the young filly on path to love her...... or do the right thing just guide young filly into being bad element of magic......
but over all I can so see Celestia training and guide young twilight to fall in love with her so when she become immortal she have a mate for ever.....

5386327
Agreed. A character's traits, personality, psyche and state of mind take a lot of consideration, and, ultimately, often reflect quite more of the other than he/she would like to admit.