- Barney finds a new wingman to replace Ted, but he's painfully shy and awkward around women. Meanwhile Ted discovers that his new girlfriend Stella hasn't had sex in 5 years.
- Ted and Stella have been dating for two months, and things are going well except they haven't slept together yet. Ted isn't too concerned as he wants to do it with her only when the time is right for both of them. But he learns from Stella that she is indeed a bit apprehensive about doing it since it's been five years since her last sexual encounter. This fact makes Ted also a little apprehensive since he's afraid that he won't measure up to her five year old expectation, so Marshall tells Ted to lower her expectation. But when they do decide that the time is right, Ted may have jeopardized the opportunity. Meanwhile, Ted still isn't speaking to Barney since he slept with Robin. As such, Barney is looking for a new wing man to replace Ted. He thinks he has the pick of any bro, but he ends up having only one applicant, his overly enthusiastic but slightly nerdish co-worker Randy. Barney thinks he can overcome Randy's shortcomings to make him the best wing man ever. It isn't until Barney learns of something in Randy's past that he truly does believe it.—Huggo
- Ted decides that it is time for his relationship with Stella (Sarah Chalke) to take the next step (they have been dating for 2 months and they haven't had sex yet.. Ted has been dry for over 5 months now). Stella is strangely reluctant, however, and she tells Ted a secret: she has not had sex for five years. Ted shares this with Marshall and Lily, as he does everything.
Lily says her longest dry streak was the summer when she was in SFO, 2 months and 19 days away from Marshall. An earthquake hit SFO and vibrated Lily enough so that she had an orgasm. Marshall tells Ted to lower Stella's expectations in the build up to the big day. Ted brings potato skins to Stella at lunch and says that he hasn't had skins in while and remembers them to be the tastiest treat ever. Ted then remarks that the potato skin, while good, is not nearly as good as the ridiculous expectation he had built up for it in his head. Stella sees right through it.
When Stella comes over on the night that she was meant to have sex with Ted (Her sister was driving in to baby sit Lucy (her daughter) and Ted had booked a hotel room for the night), they accidentally reveal that they know her secret. Stella is upset that Ted betrayed her trust and breaks up with him.
Robin is perplexed that Ted is mad at Barney, but not with her. Ted says that he has forgiven Robin and outgrown Barney as a friend. Ted has moved on.
Meanwhile, Barney tries to find a "Rebound Bro" to whom he can be a wing-man to help him get women. He misses Ted and, unwilling to admit it, puts applications up on his blog. Receiving few responses except for an enthusiastic proposal from his colleague Randy (Will Forte) (Barney says that the job is the Vice President of awesome and calls Randy the Assistant Undersecretary of only OK), Barney resorts to calling up old friends and previous wing-men. After many unsuccessful attempts (one already has a wing-man, one is married and has settled down, one has had a daughter just that very day) he decides to be the "Bro" to Randy and give him a chance. Unfortunately, he discovers that Randy hasn't had sex in thirteen years and Barney is repeatedly unsuccessful at getting him together with a woman, since Randy is uncomfortable with talking to women, and gets nosebleeds whenever he gets an erection.
Barney is unsuccessful (he even teaches 3 ways to converse with women: Isolate her from her friends, repeat her name in conversation, subtly put her down) (Randy still doesn't learn and tells a Koala loving animal enthusiast that Koala meat is delicious) until he enlists Robin's help to make Randy comfortable with small-talk with women, telling Robin that he may have a sex tape with her to convince her to come and help Randy. Barney discovers that Randy was a police officer, albeit one that was fired for incompetence; nevertheless, Barney knows being in the 'force' impresses women, and quickly finds a woman who takes Randy home with her. Barney seems happy until Robin comments that "Ted doesn't know what he's missing". Barney tearfully remarks, "You had to mention Ted, didn't you?"
Stella comes to Ted's house and admits that she broke up with him because she was afraid it was getting too serious and she was looking for a reason not to get too close to him. Ted and Stella's relationship goes even further than expected as Ted meets Stella's daughter and gets to know her. Later, Stella tells Ted that her sister (who was previously meant to take care of Stella's daughter while Stella and Ted had sex) is still in town and can take care of Stella's daughter. Stella and Ted rush to a motel, where they finally consummate their relationship. When Ted jokingly picks up the phone to tell Marshall and Lily about it after the deed is done, Stella pushes him off the bed in an equally lighthearted manner.
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