- Ted is excited when a matchmaking service claims to have found his soul mate, but he postpones his date to help Lily, who has a surprising revelation.
- It's Ted's 28th birthday and he still keeps looking for the perfect girl. Apparently he is about to find her since the matchmaker he once hired to find him a partner has finally found the perfect match. When he is about to meet her, Lily calls him because she is in trouble. Marshall gets himself into an office war between Barney and some guy named "Clark Butterfield" in which the guys do all kinds of gross things to each other.—Anonymous
- Marshall hates his internship at Atrucell, and Barney doesn't make it any easier. But things change for Marshall when he gets caught up in Barney's continuing feud with Clark Butterfield, someone who Barney can see from his own office across into another office building. Meanwhile, it's Ted's twenty-eighth birthday. He gets an unexpected present when he's contacted by Love Solutions, Ellen Pierce's former matchmaking company with who Ted signed up six months earlier. They've found his soul mate. After reading this woman's file, Ted is convinced that she is indeed his soul mate. But on what is supposed to be their first date, Ted gets an emergency telephone call from Lily, who needs his help. As Ted helps Lily out with her problem, both Ted and Lily come to some realizations about what they individually want in life.—Huggo
- Marshall hates his internship at Atrucell (The job that Barney got him, and Marshall took as he needed the money), and Barney doesn't make it any easier. But things change for Marshall when he gets caught up in Barney's continuing feud with Clark Butterfield, someone who Barney can see from his own office across into another office building (works at Nicholson, Hewitt & West). Barney and Clarke do increasingly gross things to each other & now Barney has pulled Marshall in to help him out in his feud with Clarke. Barney gives Marshall the title of "Executive mischief consultant".
Meanwhile, it's Ted's twenty-eighth birthday. Barney's present to Ted is the "greatest pick up line ever", which is to call 911 for a beautiful girl as Barney tells her that "she must have internal bleeding" as "she is an angel that fell straight out of heaven".
Ted describes his perfect girl to Lily (attractive, college educated, wants 2 kids, likes dogs, Otis Redding, likes crosswords, into sports, plays the bass guitar), who says that Ted is never going to meet anyone who meets all the criteria that Ted has set out. Ted gets an unexpected present when he's contacted by Bob from Love Solutions, Ellen Pierce's former matchmaking company (which was bought out by a high-end meats and textile conglomerate who wanted to diversify) with whom Ted signed up six months earlier. They've found his soul mate. After reading this woman's file, Ted is convinced that she is indeed his soul mate. But on what is supposed to be their first date, Ted gets an emergency telephone call from Lily, who needs his help.
Lily has found out about an art fellowship in San Francisco, and decides to apply, even though it could ruin the wedding plans. She is forced to reveal her plans and call Ted when a tire on Marshall's car goes flat near Dutchess county on her way to the interview. Ted takes a cab to meet Lily. She tells Ted that she is still having doubts about marrying Marshall and wants to see if she can get into this art fellowship and see what happens. Lily tells Ted that she is really nervous about the wedding and specifically that marrying Marshall means giving up on all the dreams Lily had to roam the world and become a painter. Lily claims that she only wants to find out if she can get in or not.
Ted tries to convince her not to go to the required interview in New Haven. Lily knows it is a mistake but she has to know for sure if she can do it, and leaves Ted on the side of the road quite far from town. Ted sends her an angry message but reminds her to pick up milk on the way home. He calls Barney, but Barney puts Marshall on the phone and Ted claims it was a prank because he does not want Marshall to know why he was all the way out in Dutchess County.
She tells Ted that a few weeks ago, she enrolled for an art course in SFO and now she has been accepted. The course means that Lily can't marry Marshall just yet. Lily is terribly conflicted between her love for Marshall and her fear of not having lived her life. Once Ted fixes the flat, Lily leaves Ted to go and attend the art course interview, which is what she was doing out there in the first place. Ted calls Lily and leaves her a message to bring Milk when she gets back home.
Finally Ted gets Robin to come to his location and pick him up. As Robin drops Ted at McLaren's to start his date with his perfect match, Ted realizes that Robin is the only perfect girl for him. Ted goes home and finds Lily talking to Marshall. Lily tells Ted that she got the "Milk" (milk standing for admission at the art course). Ted tells Marshall that he didn't go on his date as he wants Robin. Marshall says to Ted that it's a mistake, but Ted replies that it's a mistake he has to make (basically giving his blessings to Lily to go for the art course).
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