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What made her memorable: Rachel was perhaps the first woman who really threatened Don's marriage to Betty.
That's because she was smart, business-savvy, and classy as fuck.
First (and only) appearance: Season 4, Episode 6, "Waldorf Stories"Don's relationship status at the time: Divorced from Betty. She's a waitress whom Don meets after the CLIO Awards.
Even Don doesn't remember meeting her, and he wakes up next to her!
What made her memorable: In general, Betty just gives zero fucks and it's so wonderful.
Whether she's humping a dryer, shooting her neighbor's prized pigeons, or sucking whipped cream from a can — she is number one, always.
What made her memorable: This was a sad sort of romance, in that Megan viewed Sylvia as a friend, and Sylvia was cheating on her hardworking doctor husband with Don.
In fact, her father walked in on them post-coital, and as a viewer, you may have vommed in your mouth a bit.
First appearance: Season 4, Episode 1, "Public Relations"Don's relationship status at the time: Freshly divorced from Betty.
What made her memorable: Candace is the prostitute who slaps Don during sex, and then he asks her to do it "harder," and then everyone watching died a little from happiness.
First appearance: Season 1, Episode 1, "Smoke Gets in Your Eyes"Don's relationship status at the time: Married to Betty and also sleeping with Midge.