- Barney helps Abby get back at Ted by staging a fake proposal, but Abby doesn't realize that it's fake. Lily decides to sell some of her paintings so that she and Marshall can pay for floor repairs at their new place.
- Since Marshall and Lilly cannot afford the cost to level the floors of their new place, Marshall proposes its time to start selling some of Lilly's designer clothes. Lilly instead wants to make the money selling her paintings which takes her to some low places. Ted tries for an interesting look while Barney finally meets the girl that has been ruining his chance with women.—Andrew
- Barney finally finds out which of his past conquests has been stalking him then badmouthing him to other women: Abby, Stella's naive receptionist with who Barney slept with once and never called again. But in their subsequent conversation, they come to the realization that they both have a common "enemy": Ted, despite the fact that both still really love him. Abby is still hurt that Ted bypassed her in favor of Stella. So Barney and Abby decide that they should show Ted that his quest for true love (for Barney) and his quest for true love with Stella (for Abby) is stupid. But the plan takes a turn for naive Abby. Meanwhile, Marshall has some bad news for Lily. The cost for the work on their new apartment is much higher than they expected. With Marshall still out of work, he thinks the only way to pay for the work is to sell Lily's designer clothes. Lily comes up with another plan: she can sell her paintings. Marshall lets it slip that he doesn't believe in her as an artist. Lily tries to prove him wrong.—Huggo
- Marshall and Lily face a dilemma when they discover that fixing the slanted floor in their new apartment will cost an additional $1,500. To raise the money, Marshall suggests selling some of Lily's designer clothes on a website. However, Lily playfully counters with a humorous suggestion to name the website similar to a guy forcing his wife to live in a garbage bag for the next three years, only to find out that the site already exists. As an alternative, Lily proposes selling her paintings, but Marshall unintentionally insults her by questioning their quality, claiming that people only pay for "real" paintings. Hurt by his comment, Lily decides to take matters into her own hands and sell her artwork within a week.
Meanwhile, the gang engages in a discussion about Ted's seldom-worn red cowboy boots. They believe Ted doesn't have the style to pull them off, but Ted is determined to prove them wrong.
Lily's attempts to sell her paintings prove to be challenging as she tries various venues, starting with an art gallery, then a local coffee shop, and finally ending up at the local flea market. After several failed attempts, her painting is eventually bought on the street by a couple known as G-CWOKs (Gay Couple Without Kids), who are influential in the art world. Excited by the sale, Lily contacts the G-CWOKs to discuss hosting an art party to sell more of her work. However, her excitement turns to devastation when she learns that the couple only bought her painting because of its vintage and valuable frame. To make matters worse, they confess to throwing away the actual painting.
Marshall and Ted confront the G-CWOKs, Lawrence and Walter, who surprisingly appreciate Ted's red cowboy boots, proving that he can indeed pull them off. One of the G-CWOKs even develops a crush on Marshall, as Marshall has a strong appeal among gay men. This encounter leads them to a nearby veterinarian's office, where they meet Dr. Greer, the veterinarian. Dr. Greer had discovered Lily's discarded painting in the dumpster and hung it up in Examination Room 3. To his surprise, the painting has a calming effect on the dogs being examined, though birds show no interest in it. Impressed by the impact, Dr. Greer offers to buy several of Lily's paintings that would be enough to cover the cost of fixing the slanted floor. Inspired by this opportunity, Marshall creates a website where Lily can sell more of her artwork to other veterinarians.
Meanwhile, Barney continues to deal with a mysterious woman who has been sabotaging his attempts to seduce women by revealing his true intentions. Each time Barney's intentions are exposed, he receives a slap from his target. Determined to uncover the identity of this saboteur, Barney follows her from the bar to a taxi, only to discover that it's Abby, Stella's secretary. Abby confesses that she is in love with Ted and is hurt that he chose Stella over her. Barney seizes the opportunity to vent his frustrations about Ted, as he feels betrayed by their friendship. In a twist, Barney and Abby end up sleeping together again.
Barney and Abby devise a plan to expose Ted's negative behavior in relationships. They decide to wear matching blue sweaters and announce that they are dating, with Abby unable to hide her lingering feelings for Ted. Ted becomes suspicious and warns Barney to stop, but Barney takes the prank to the next level by proposing to Abby. Unaware that it's part of the plan, Abby excitedly accepts the proposal and rushes off to share the news with her mother.
Later, Barney visits Abby's apartment to retrieve a tie he claims to have left behind, only to find Abby already discussing wedding plans. Realizing he needs an excuse to back out, Barney tells Abby he can't marry her because he made a promise to Ted. He falsely asserts that Ted is still in love with Abby, providing her with Ted's address and suggesting she visit him at 2 am since Ted often works late.
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