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Thomas Kessler is the handsome and charming CEO of a high-end  furniture design company that has been a longtime client of Zane Specter Litt Wheeler Williams. When he returns to the firm for help, Donna steps in to assist, but in doing so also catches his eye, as he and Donna hit it off and he asks her out on a date after she solves a problem for him. She initially declines, but accepts after some encouragement from Gretchen.

They eventually go out on a date and start a relationship. Donna tells Louis about it, but doesn't tell Harvey until he sees Thomas arriving at the firm to pick her up for a date. In business, Thomas is fair and honest, which leads to him accepting a deal from Harvey's client and then backing off once Donna learns that the client only wanted Thomas's deal to get a better one from a competing business. Because Harvey told Donna and broke privilege, the firm gets sued and Harvey almost loses his license to practice law, during which process he asks Thomas to lie in court in order to save Donna, and not himself. Due to that, Thomas sees what Donna means to Harvey, and asks what Harvey means to Donna, and it is presumable that their relationship is over when Donna admits to Thomas she can't cut Harvey out of her life.

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