Bertram, who becomes Count of Roussillon at the beginning of All’s Well That Ends Well upon the death of his father, is young, and has all of the arrogance that youth can bestow, especially on someone as privileged as he is. The young count might be compared to a number of Shakespeare’s earlier young and naïve male characters, such as Claudio from Much Ado about Nothing (who spurns his beloved, Hero, at the altar because he’s been led to believe she’s been unfaithful). He is gullible, looking up to his general, Parolles, and then disowning him when Parolles is proved to be a coward. He displays snobbish attitudes towards the lower-born Helena, a ‘poor physician’s daughter’, and even offers her low-born status as one reason why he doesn’t want to marry her. And, of course, he seduces Diana without a thought for her or her honour, abandoning her once he’s lain with her. Like so many 
people who have had everything handed to them on a plate thanks to their privilege and their birth, he thinks he can just deny all of the charges at the end of the play and get away with it, until Helena appears with the undeniable evidence (the ring, and her pregnant belly).
This may make him sound like a character it would be difficult to feel much sympathy for. But the plot of the play – and in particular, the central point around which the plot pivots, namely Bertram’s forced marriage to Helena – makes it hard not to feel some sympathy for a young man who has been coerced by his King, no less, into marrying a woman he does not love.
As we remarked in our analysis of the play, Bertram has been tricked into accepting Helena, a woman he never sought for his wife in the first place; but on the other hand, he needs to be punished for his treatment of Diana, whom he has dishonoured. In All’s Well That Ends Well, Bertram is a cad for seeking to seduce Diana when he has no plans to make an honest woman of her, but at the same time, he never wanted Helena in the first place and was forced to marry her. The seemingly impossible impositions he lays down for her, involving the ring and the pregnancy, are extreme, but he has some cause for being unhappy about the King forcing him to accept Helena as his bride. Helena, too, in requesting him, knowing that the King will not refuse her, is less than morally pure.
In the last analysis, Bertram is immature and entitled, and one can’t help feeling he could benefit from being taken down a peg or two, like his friend Parolles and the humiliating ordeal he undergoes with the soldiers. There is a suggestion that Helena is needed to ‘tame’ or educate him: although she has forced and then tricked him into the marriage, he does seem to accept her as his wife graciously and readily at the end, suggesting that progress has been made and a happy union may result: ‘If she, my liege, can make me know this clearly, / I’ll love her dearly, ever, ever dearly.’ This last line goes a little further than ‘if she’s proved right, I’ll throw up my hands and admit defeat’. And one of the other things we should bear in mind is that, although he was tricked into sleeping with Helena, believing her to be Diana, he didn’t notice the difference while they were making love. (Just how dark was it when these people ended up bedding each other in these ‘bed tricks’, one wonders? They never seem to notice that the person they’re with looks and feels different from the person they thought they were with. Dramatic licence, one supposes.) Bertram’s character is revealed at the end of the play, then, to have mellowed slightly, leaving the possibility that he and Helena will have a good marriage despite the circumstances under which they were put together.