Emma Frost has some pretty famous exes: Namor, Tony Stark and most notably, Cyclops. However, she also might have been on a few dates with Bruce Wayne before joining the X-Men — or Bruce "Gotham," as she calls him.
In Karl Kesel and James Fry's story in 2002'S X-Men Unlimited #34, Emma Frost goes on a date with a millionaire named Bruce during a vacation in Monte Carlo. An obvious tongue-in-cheek Batman reference, Emma never actually divulges his full name. She says, "This time it's...well, let's just call him Bruce Gotham."
The story takes place after her run on Generation X but before she officially joins the X-Men. As such, Emma grapples with her conscience over killing her sister, Adrienne Frost. Adrienne and Emma weren't exactly a happy family, and it was actually Adrienne who was responsible for the deaths of several children, most notably, Everett Thomas, aka Synch. Synch's death crushed Emma and, in a moment of retaliation, she shot her sister point-blank with a gun, instantly killing her.
Of course, Emma wasn't too interested in dating Bruce to begin with and was, instead, simply trying to escape the demons of her past by living life lavishly. She says, "I don't even bother to read his mind. I didn't come here to be bored." Fortunately for her, Bruce decides to leave in the middle of the night, leaving his suite for her as "long as she wants it." Of course, the book doesn't actually call him Bruce Wayne because of obvious copyright issues, but one can assume this Batman stand-in was probably headed off to fight crime in Gotham. There's a bit of humor in the knowledge that if this was really Bruce Wayne and Emma had read his mind, maybe she would have found out he was a lot more interesting than she ever gave him credit for.
It's also fair to assume that had this really been Bruce Wayne, this meeting would have been between two master manipulators, each using the other as a means to an end. Bruce needs to keep up his playboy persona while Emma simply wants to live life lavishly—and get some diamond necklaces from hopeful millionaires while she's at it.
The rest of the issue is an interesting look into Emma's psyche. After Bruce jets off for New York, Emma deals with the ghost of her sister. She remembers her students, thinks back to the bombing incident Adrienne had a hand in orchestrating and how she shot her sister in cold blood. Speaking to the illusionary version of Adrienne that she sees, Emma finally says, "People suffered. People died, I'm not sorry I killed you, Adrienne...I'm sorry I didn't kill you a lot sooner." She takes the gun (the same one she used to shoot her sister) and fires it directly at "Adrienne."
Afterward, Emma reflects, declaring that she's gone soft and because of it, students like Everett and the Hellions, lost their lives. "Never again. From now on I'll be hard. As diamonds," she says, putting on the diamond necklace Bruce gave her earlier in the night. It's a powerful nod to the fact that when she finally appears in New X-Men, she'll have a new diamond form. However, by that time, the cold hardness of her diamond form—and the equally icy facade she's put on—don't protect her from the emotional pain of losing more students.