Asher is introduced in Desperately Seeking Serena when Jenny Humphrey, sick of being overlooked by Blair, decides to find a boyfriend to show her up. She originally meets Asher when one of his dogs causes her to drop her hot dog, and he gives her his number. She isn't interested at first, as she thinks she deserves a guy with more status than a dog walker. Soon after, she and Elise Wells spot Asher delivering his dogs to be walked by someone else and realize he owns the dogs. After this, Jenny and Asher grow closer. They make plans for a lunch date in the park, but Rufus Humphrey forbids her to go; due to her still being grounded after the events of her birthday. After she cancels, Asher shows up at the loft with a bag of hot dogs so they can still hang out.
In All About My Brother, Asher and Jenny have officially started dating. They're moving quickly, and Dan Humphrey voices his concerns to Serena van der Woodsen, who encourages him to get to know Asher. Before school one day, Dan sees Asher kissing a mystery guy. He confronts Asher about it, and he readily denies it, threatening to take Jenny's virginity. That night, he and Jenny plan to co-host a party at his house together. Meanwhile, Jenny lies to her friends that she and Asher have consummated their relationship and tries to get him to sleep with her to make it true. He refuses, and tells her that she is nothing more to him than his beard and he's willing to keep being her nice boyfriend for show if she keeps quiet. At the same time, Georgina Sparks outs Eric van der Woodsen as being gay, and he admits to Serena that he met Asher at The Ostroff Center and they started dating. At the party, Blair Waldorf brings Asher back his phone that she had her minions steal, and after receiving permission from an angry Eric van der Woodsen, she forwards all their texts to Gossip Girl. Asher is officially outed as being gay, and Jenny is confronted about her knowing Asher was gay and lying about how far they went. This is Asher's last appearance in the series.