What I Like About You Wiki
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Holly Tyler Gary


Michael McMillian

Henry Gibson (portrayed by Michael McMillian) is Holly's first love and first boyfriend. He becomes friends with Gary and Vince and is known to be a likeable, insightful, and intelligent person. While he is socially awkward and shy at first, he gradually becomes more assertive and confident, especially through his relationship with Holly.

Holly and Val first meet Henry in a men's bathroom at B-91 during a girls' night out where Val, playing wingman for Holly to attract a guy, is kissed by Holly's intended target. Distraught, Holly tries to escape Val in the men's bathroom only for Val to follow her in there. There, Henry almost uses the bathroom in front of them as Holly and Val are talking.

Val attempts to mend Holly's broken heart by having her meet Henry, whom Holly politely refuses. However, so that Gary wouldn't be alone and dumped by his girlfriend on Valentine's Day, Holly agrees to going a fake date with Henry (as part of a double date with Gary and Jill). During the date, Henry impresses Holly with his hypothetical proposal of marriage to her (he said he would propose to Holly at a garbage dump, so when she felt sad, he could remind her of the event to cheer her up). The two became a couple.

Henry becomes jealous of Holly's friend Vince, who Holly explained that he shouldn't be jealous of which caused her to blurt out (and eventually take back) "I love you." When he learns that Holly has feelings for Vince, Henry breaks up with her and eventually moved on with a girl named Kate. Henry and Holly retain a friendly relationship, though she worries about Henry's happiness as a result of her own feelings for Vince, and he continues to help her out, particularly when he helps her rewrite an essay to get a summer internship in Paris. Henry ends up breaking up with Kate when she questions his feelings for Holly after they overhear Holly and Valerie fighting over Holly's feelings for both Henry and Vince.

Still having feelings for her, Henry kisses Holly twice before her summer trip to Paris. He and Vince wait the entire summer for Holly to return and finally choose between the two. However, his hopes of winning her back are dashed when she returns with a new boyfriend, Ben, a musician from Britain. He and Holly manage to part amicably before he leaves for Princeton, when Holly tells him that he is her first love. When she sees him again, Henry has settled into college life, joking somewhat darkly that his friends don't call, and dates a girl coincidentally named Holly.