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As this question shows we don't know much about Robb and Jeyne's wedding. However, what is clear is why Robb decided to wed in the first place...

"I took her castle and she took my heart." Robb smiled. "The Crag was weakly garrisoned, so we took it by storm one night. Black Walder and the Smalljon led scaling parties over the walls, while I broke the main gate with a ram. I took an arrow in the arm just before Ser Rolph yielded us the castle. It seemed nothing at first, but it festered. Jeyne had me taken to her own bed, and she nursed me until the fever passed. And she was with me when the Greatjon brought me the news of . . . of Winterfell. Bran and Rickon." He seemed to have trouble saying his brothers' names. "That night, she . . . she comforted me, Mother."

Catelyn did not need to be told what sort of comfort Jeyne Westerling had offered her son. "And you wed her the next day."

He looked her in the eyes, proud and miserable all at once. "It was the only honorable thing to do. She's gentle and sweet, Mother, she will make me a good wife."

A Storm of Swords - Catelyn II

So Robb bed a woman... so what? Why did he feel he needed to marry this woman? This is what got me thinking if Robb had bed other women prior to Jeyne. I know the Starks are full of honor, but being around Theon who beds whores like its his job, and being raised with Jon whom was born out of wedlock by their own father (or so everyone believed), surely Robb would not have had that impression right?

I see basically two options 1) Robb and Jeyne were both virgins and somehow this affected the decision or 2) because Jeyne is highborn different rules apply than whores or tavern wenches. So to bring it full circle...

Was Rob Stark a virgin prior to when he met, bed, and married Jeyne Westerling?

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There is nothing explicitly mentioned in the books regarding Robb's love life prior to Jeyne Westerling but there are implications that go both way.

First of all we have to see his relationship with Theon Greyjoy. Theon and Robb were best friends and as close as brothers to each other. Theon was no stranger to bedding serving girls and he and Robb apparently used to discuss the girls afterwards. The passage cited below, describing one such instance.

Two serving wenches stood beneath the sign of the Smoking Log, the local alehouse. When Theon Greyjoy called out to them, the younger girl turned red and covered her face. Theon spurred his mount to move up beside Robb. "Sweet Kyra," he said with a laugh. "She squirms like a weasel in bed, but say a word to her on the street, and she blushes pink as a maid. Did I ever tell you about the night that she and Bessa—"

"Not where my brother can hear, Theon," Robb warned him with a glance at Bran.

Bran looked away and pretended not to have heard, but he could feel Greyjoy's eyes on him. No doubt he was smiling. He smiled a lot, as if the world were a secret joke that only he was clever enough to understand. Robb seemed to admire Theon and enjoy his company, but Bran had never warmed to his father's ward.
AGOT - Bran V

It looked like Theon had forgotten that Bran was with them and Robb didn't want him to listen to all the adult talk. Now this can be interpreted both ways. One could be that they used to share their exploits with each other. Or that Robb was that one virgin friend who loves to listen his best friend talk about his sexual conquests. Jon Snow was Robb's best friend too but Jon's much more solemn in nature and has an aversion to anything that leads to making bastards due to his personal experiences, so it is understandable why he was not included in these talks. Not to mention, Jon never got along with Theon.

Then we have Catelyn's account which implies that serving girls in Winterfell were very much attracted to Robb, the young heir to the North.

Robb got to his feet slowly and sheathed his sword, and Catelyn found herself wondering whether her son had ever kissed a girl in the godswood. Surely he must have. She had seen Jeyne Poole giving him moist-eyed glances, and some of the serving girls, even ones as old as eighteen … he had ridden in battle and killed men with a sword, surely he had been kissed. There were tears in her eyes. She wiped them away angrily.
AGOT - Catelyn XI

They were not the only ones, Princess Myrcella kept staring at Robb during the feast at Winterfell and Robb was grinning like an idiot when he got to escort Myrcella to her seat prior to that. It was as if he (13?) had never had a girl (8-9?) touch his arm before. But just the fact that Jeyne Poole or serving girls were interested in him doesn't really say if Robb returned their affections. Nor does the thing with Myrcella who was way too young and probably didn't understand all that anyways.

Finally we have his one explicit sexual encounter, that was with Jeyne Westerling.

"I took her castle and she took my heart." Robb smiled. "The Crag was weakly garrisoned, so we took it by storm one night. Black Walder and the Smalljon led scaling parties over the walls, while I broke the main gate with a ram. I took an arrow in the arm just before Ser Rolph yielded us the castle. It seemed nothing at first, but it festered. Jeyne had me taken to her own bed, and she nursed me until the fever passed. And she was with me when the Greatjon brought me the news of . . . of Winterfell. Bran and Rickon." He seemed to have trouble saying his brothers' names. "That night, she . . . she comforted me, Mother."

Catelyn did not need to be told what sort of comfort Jeyne Westerling had offered her son. "And you wed her the next day." He looked her in the eyes, proud and miserable all at once.

"It was the only honorable thing to do. She's gentle and sweet, Mother, she will make me a good wife."
ASOS - Catelyn II

This folly seems to imply that Robb was not used to bedding women and then leaving them at all and Jeyne might as well have been his first. He risked his life, his family and his kingdom for the "Honourable thing", something you don't expect a man, well let's say more experienced in the ways of the world, would. Of course there's a possibility that he genuinely fell helplessly in love with her, but he doesn't mention that emphatically when he gives his reasons to his mother. If it was all about love, he would not have mentioned how she comforted him and he had no other choice. It is also possible that Jeyne was the first noble woman he had laid with, the first one with whom he could hope to have a future so she was different from serving girls and peasants. But it still doesn't make sense to lose everything for her. To quote Jaime:

She did not look dangerous. Jeyne was a willowy girl, no more than fifteen or sixteen, more awkward than graceful. She had narrow hips, breasts the size of apples, a mop of chestnut curls, and the soft brown eyes of a doe. Pretty enough for a child, Jaime decided, but not a girl to lose a kingdom for.
AFFC - Jaime VII

That's what Jaime says on the matter, a guy who is hopelessly in love and has never been with anyone except one woman and even he realises how much of a folly was it. That's absolutely not something you expect from a man who is used to do that.

So in conclusion, there is no conclusive and explicit evidence for or against this. Robb may or may not have been a virgin. The evidence, or lack thereof, compels me to argue that until better evidence appears, we should assume that he was a virgin.

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    Hmmm. I thought he would have at least done it for the huge tracts of land, but Jaime's quote indicates otherwise.... – Skooba Nov 1 '18 at 13:12
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    “Or that Robb was that one virgin friend who loves to listen his best friend talk about his sexual conquests.” Or that Theon loves to talk about his sexual conquests, and his honourable brother Robb humours him. – Paul D. Waite Nov 1 '18 at 17:08
  • @Skooba Jaime's description is actually something of a contradiction in the text. Catelyn twice refers to Jeyne's hips as "good". I guess Cersei's are just somewhat larger and make Jeyne's look very narrow in comparison... – A Simmons Nov 1 '18 at 17:43
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    I would also consider that Robb might believe there is much more commitment required (by "honor" or social convention) when sleeping with a daughter of a lord than when sleeping with a serving girl. – The Photon Nov 1 '18 at 18:01
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    A point of clarification: the fact that he considers marrying Jeyne to be "the only honorable thing to do", and had not previously felt he had to marry a serving girl for the same reasons does not necessarily imply anything. Ladies have honor that can be besmirched; serving girls don't have any in the first place. – thegreatemu Nov 1 '18 at 20:10
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We are never given any indication that Robb wasn't a virgin, and I feel that we're expected to assume he was. Robb is 14 at the start of AGOT, so he's only a couple of years into puberty, which means he hasn't really had a lot of time. Robb does not live in a large city where he could easily visit a brothel without everyone knowing, and in general his role models would disapprove of this behavior. Theon is an exception, but Robb definitely based himself more on Ned.

I also think you're completely misreading the effect Jon would have had on Robb. Ned was certainly not proud of having had a bastard; the fact that he never had an affair again would have made people think it was a decision in his youth he regrets and I feel Robb would have seen the issues Jon had fitting into the family. Jon's example would have made Robb less likely to risk fathering a bastard, not more. If that happened, he's be left with the choice to support the child, as Ned did, and see the issues with Jon play out in his own future marriage, or abandon the child, which would certainly be dishonorable.

As to why Robb married Jeyne, it is extremely different to sleep with a highborn woman than with a lowborn one. If it got out that Jeyne was not a virgin it could easily have ruined her life. Many would refuse to marry her based on that, and her family is poor and not very powerful, so there's likely nothing they could do to make her more appealing. If she had a bastard it would be even worse for her. Really the only way to stop this from negatively effecting Jeyne would be to marry her, and Robb is a decent enough person that he couldn't face abandoning her. Falling in love with Jeyne would also have contributed to this.

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