In Mrs. Dalloway, why did Clarissa marry Richard instead of Peter, and does she regret it?

Quick answer:

Woolf is posing the question of whether we are essentially who we were as children. Clarissa has had a very privileged childhood, but that childhood has left her with a desire for stability and security, which manifests itself in her choice to marry Richard Dalloway instead of Peter Walsh. Clarissa and Richard have suffered through one major loss (the death of their son), so it's easy to imagine that the couple would be satisfied with their lives together—but Woolf implies that they may not be truly happy. The question remains: would marrying Peter have made Clarissa happier? We'll never know.

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Clarissa Dalloway spends much of the novel reminiscing about one eventful summer at Bourton—her childhood country home—when she was a teenager. It was here that the most significant characters in the novel (Peter, Clarissa, Richard Dalloway, and Sally Seton) spent time together. In many ways, the novel asks and answers the question: to what extent is who we are as adults determined by who we were as children? Woolf introduces Bourton with nostalgia and foreboding, as early as the first page:

For so it had always seemed to her, when, with a little squeak of the hinges, which she could hear now, she had burst open the French windows and plunged at Bourton into the open air. How fresh, how calm, stiller than this of course, the air was in the early morning; like the flap of a wave; the kiss of a wave; chill and sharp and yet (for a girl of eighteen as she then was) solemn, feeling as she did, standing there at the open window, that something awful was about to happen.

There is loaded language here that suggests beauty, innocence, and danger.

The essential tension at the summer home is that between tradition and change. Sally Seton embodies a new, bohemian, liberal freedom, while Clarissa's family represents traditional mores. Like Sally, Peter challenges Clarissa, asking her to think deeply, to question, and to rebel against snobbery and rigidity. However, the calm, certain, stable, comfortable future promised by Richard Dalloway proves to be the better choice to her.

Years later, of course, Clarissa still thinks about this choice. She has deep, complicated feelings for Peter but suggests that he would have loved her too intensely for the marriage to be a success.

She thinks:

So she would still find herself arguing in St. James’s Park, still making out that she had been right—and she had too—not to marry [Peter]. For in marriage a little licence, a little independence there must be between people living together day in day out in the same house; which Richard gave her, and she him. (Where was [Richard] this morning for instance? Some committee, she never asked what.) But with Peter everything had to be shared; everything gone into.

She feared the prospect of a relationship with Peter due to the ardency of their connection, but Richard is also the safer bet financially. Peter never finished college and has been less stable—and certainly less rich—which matters to Clarissa (even if she would struggle to admit it). Peter's critique that she is a "perfect hostess" cuts to the bone because he's so right. Clarissa is most comfortable with gaiety, frivolity, enjoyment, and superficiality. A relationship with Peter would have been a passionate disaster.

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The relationship between Clarissa Dalloway and Peter Walsh is one of the most important components of Mrs. Dalloway

Peter and Clarissa had once been good friends. They were very intimate and familiar with each other. Apparently, Peter could "see through" Clarissa, an extremely powerful trait in a novel in which everyone is constantly positioning, posturing, and performing in a complex social milieu. Clarissa, a high-society woman, is particularly adept at playing this game. 

Peter remembers of their friendship: 

"They had always had the queer power of communicating without words. She knew directly he criticized her. Then she would do something quite obvious to defend herself... but it never took him in, he always saw through Clarissa." 

It is suggested in the book that this was the reason Clarissa rejected Peter: he made her feel vulnerable, by "seeing through" her performances.

Clarissa instead chose to marry Richard Dalloway, a reliable, if unimaginative, man. In the novel, they don't share the intimacy that she shared with Peter, which is something she both longs for and fears, as that intimacy also makes her vulnerable. 

Clarissa continues to be affected by her memory of Peter. She thinks of him the morning of her party, when she believes he is still in India and hasn't seen him for many years, wondering what it would have been like to marry him. When he visits her, unannounced, that afternoon, she thinks to herself, "Now of course... he's enchanting! perfectly enchanting!", before becoming annoyed at him again, and then becoming emotional when he tells her that he's going to marry a woman he met in India. 

Peter, similarly, continues to be affected by his memory of Clarissa. He revisits in his mind the moment when he first saw her together with Richard Dalloway, and he had the "sudden revelation... 'She will marry that man'... He didn't even know his name." When he visits her, he breaks into tears.

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