Barney Stinson had his fair share of romantic flings throughout How I Met Your Mother, but he dated very few women. Neil Patrick Harris portrayed the cheerfully manipulative figure for all 208 episodes of the CBS sitcom. Despite evolving when it came to his views on settling down, Barney never fully gave up his womanizing ways until he became a father in the divisive How I Met Your Mother series finale. Interestingly enough, it was yet another one-night stand that truly changed his view on life forever.
While Barney's job remained a mystery for much of How I Met Your Mother, the character spent most of his free time seducing women. As the confident and oversexed member of the core group at the center of the series, Barney was often criticized for the lengths he took in winning over girls for brief flings. In fact, Barney even had a playbook that he used as a manual in how to score with women, and surprisingly, the plays usually worked.
Despite Barney's various sexual encounters over the course of the sitcom, he only had four real relationships. The rest of the women Barney encountered certainly wouldn't be classified as "dates" since he discarded them as fast as possible. Barney's first serious girlfriend was Shannon, a woman he dated in the '90s that resulted in his transformation into a businessman. Next was fellow main core character Robin, who he eventually married before the two realized the relationship wouldn't last for the longterm. In addition, Barney fell head over heels for Nora, Robin's co-worker, and Quinn, a stripper he was once engaged to. There were, however, a handful of other memorable female characters that Barney encountered.
Barney had a few interactions with Wendy, the waitress at MacLaren's Pub, on multiple occasions. Since she was clearly infatuated with him, Barney worried about her reaction after he broke things off, including the belief that she wanted to poison him. Aside from Wendy, Barney also hooked up with the pub's bartender, Karina. He also manipulated Abby, the receptionist at Stella's dermatology office, played by Britney Spears. Barney also had an affection for older women since he had encounters with Rhonda (aka "Man-Maker"), Professor Lewis, elderly Mrs. Buckminster, and Madeleine Albright. With the dozens and dozens of women that he slept with, it was the end of the perfect month, or "Number 31," who made Barney a father.
Though Barney found a lot of success when he tried to seduce women, he also failed on a few occasions. He never had a chance with Lily despite his persistent demeanor. Barney also tried and failed when it came to Ted's mom, Virginia, and Ted's sister, Heather. Of course, the "Mother," aka Tracy, never gave Barney a shot in her brief time shown on How I Met Your Mother. Thankfully, his priorities changed with the birth of his daughter, Ellie.