It was hinted in season 2 and referred to in season 4 that Dana had a brief relationship with Ari Gold. In Season 5, Dana herself confirmed that she had had a sexual relationship with Ari Gold. Throughout the course of the series it became apparent that Dana still had romantic feelings for Ari. Ari implicitly revealed his continuing affection for Dana when he said (in a bit of foreshadowing) that if he ever cheated on his wife, it would be with Dana.
Dana is physically attractive, having a smoky, sexy voice, black hair, tan skin, and sparkling eyes. Strangely, she somewhat resembles, in looks and personality, Ari's wife, Melissa, helping to further explain the relationship between Dana and Ari.
Dana, at the beginning of her career in Hollywood, worked in the accounting department at Warner Bros. Although the particulars are left ambiguous, somehow Ari was able to help Dana's career, and get her a job as a studio executive. The fact that Ari helped Dana to advance in her career explains her loyalty, trust, and affection for him.
In Season 5, Ari worked his influence to get Dana the job as President of Warner Bros, and she in turn gave his client, Vincent Chase, a role in the film "Smoke Jumpers."
In season 8 it was revealed that Ari and Dana were lovers in 1992. The relationship serious, but at the time Ari was also seeing his future wife Melissa. Dana wanted to marry Ari, telling him "marry me or walk." This confrontation led to Ari leaving Dana in order to marry Melissa. Dana regretted this, as she never married afterward. As Dana got older, and gained the presidency of Warner Bros. Studio (with Ari's help) she appeared to grow more rueful about her personal life. In season 7, she asked for Ari's sperm because she "wanted a baby" as she was "pushing forty" and "didn't have a man." Dana later claimed she was kidding, but it could be inferred that the joke revealed a true desire of Dana's to start a family.
Dana had a major recurring role in season 8. When Ari separated from Melissa, he visited Dana after an awkward date with a much younger woman. This led to Ari and Dana having sex. The morning after, Dana appeared happy and content, but was disheartened when Ari told her he had a marriage counseling session with Melissa that day. That night Ari took Dana out to dinner to Bobby Flay's restaurant (Flay was dating Melissa) in order to make Melissa jealous. Dana was furious at being used, and walked out on Ari.
Ari realized he had made a mistake and tried to avoid Dana. However, this proved impossible as Dana had to go to Ari's office on business. While there, she met Ari's children, including his son Jonah, who asked her "are you the Dana our mom hates?" This caused Dana to break down, telling Ari that the situation was humiliating but that she "did nothing wrong." Ari told her that if he didn't have a family, things would not be complicated between Dana and him, but that he didn't know what to do. Later that night, Ari drunkenly called Dana, who offered to see hiim. Dana told Ari she was "lonely" and willing to take her chances on another relationship with Ari.
By the penultimate episode of the series, Ari and Dana were dating. She was spending the night with Ari at his hotel, and appeared to be content. She fixed Ari's tie, offered to help him get backing for Drama's t.v. movie, and kissed Ari on his way to work, smiling at him as he left. Yet, Ari still was not over Melissa. Sensing this, Dana asked Ari if she was wasting her time because she didn't "have time to waste." This implied that Dana was eager to start a family with Ari. Ari had to be honest, and admitted that while he had a great feeling when he was with her, he still loved Melissa. This led Dana to realize that Ari would never be able to fully love her, and she told Ari to go back to Melissa. Dana admitted that Ari's confession made her sad, but she could not be mad at Ari, because he was being honest with her. Dana then kissed Ari one last time, and left, appearing to be slightly crying (appropriately, it was her last appearance on Entourage).
- In one episode, she jokingly referred to herself as "The Vanna White" for her studio.
- Ari claimed in season 7 that if he ever cheated on his wife, it would be with Dana. This would happen in season 8, as Ari was not divorced from Melissa while he dated Dana. Thus, Ari was technically cheating on his wife with Dana.
- In season 2, Dana was portrayed as being married and having a son who attended school with Ari's younger daughter. This aspect of Dana's life was dropped, and in season 7 it was established that Dana was unmarried and had no children.
- Dana is one of the few studio executives on Entourage to be portrayed positively. She never seeks to hurt Vince or Ari's career, indeed helping both of them achieve their goals. Also, no matter how badly her business ventures with Ari went, she never stopped working with him.
- Dana never speaks to Drama or Turtle throughout the series, only ever speaking to E, Vince, and Ari (most of her scenes are with Ari).
- Throughout Entourage's run, Dana never shares any scenes with Melissa (Ari's wife). The characters speak to each other only one time throughout Entourage's 96 episodes. In the eighth episode of season five ("First Class Jerk') Dana and Melissa speak to each other on the phone. Dana says "hi" to Melissa, and Melissa answers with "hello." This is the only contact that Ari's love interests have with each other during the course of the series.
- Dana usually wears business suits.
- Throughout the course of the series, Dana is portrayed as only having female assistants.
- Other than Melissa (Ari's wife) Dana is the only character on Entourage that Ari has a romantic relationship with.
- Dana's inability to marry Ari and childlessness serve to portray her as one of Entourage's truly tragic characters.
- With the exception of Aquaman, none of Vince's projects with Dana go through. Vince's Ramones project that Dana wanted to produce is killed when her boss buys the script (this also leads to Dana being fired). Lost in the Clouds is cancelled following the disastrous reception of Medellin, and Smoke Jumpers is shut down midway through production. In season 8 it is revealed that Firewalker, Vince's super-hero movie Dana greenlit, will commence shooting in March, but it is never actually shown to be completed in the series.
- Throughout the series, Dana only kisses Ari, though Vince kisses her (on the cheek-"The Cannes Kids").
- Dana is one of the few recurring female characters on Entourage (the others being Shauna and Melissa) that Vince never propositions or has sexual relations with.
- In both Dana's first and last appearances on Entourage, she is wearing black.
- Dana is first ever mentioned on Entourage in the episode "The Boys Are Back in Town." However, her first actual appearance is in the episode "Aquamansion."
- In "Snow Job" Dana impersonates Melissa (Ari's wife) in order to get him on the phone. This could be construed as foreshadowing Dana and Ari's relationship in season 8, as it is strongly hinted in the episode "Second To Last" that Dana wants to marry Ari. It also refers to Ari and Dana's earlier relationship, when Dana proposed to Ari ("marry me or walk").
- Practices Yoga. ("First Class Jerk").
- Ari refers to Dana as the "the second love of my life."
- Dana proposed marriage to Ari in September 1992 ("marry me or walk"- "One Last Shot").
- Ari and Dana have a romantic relationship twice in their life, and each time it ends exactly the same way. Ari and Dana dated from 1990 to 1992, and the relationship ended when Dana confronted Ari to get serious with her-to either marry her or end the relationship. Ari breaks up with Dana and marries Melissa. In 2011, Ari and Dana reignite their romance. However, the relationship ends when Dana once again confronts Ari about getting serious with her. Ari and Dana then break up, and Ari goes back to his wife Melissa.
- Dana does not appear in seasons 1, second part of season 3, or season 6.