Before the senior dance , Tom invite his ex @-@ wife Wendy ( Jama Williamson ) to his office to finally disclose his romantic feelings for her , but she reject him . Not satisfied with the outcome , he attempt to blackmail her into a date using an alimony lawsuit as leverage . Tom and Wendy are later shown hugging and presumably making amends , although their conversation remain inaudible . Meanwhile , April 's ( Aubrey Plaza ) boyfriend Derek ( Blake Lee ) and his boyfriend Ben ( Josh Duvendeck ) mock the senior citizens , causing April to question why their interactions must constantly be " cloaked in like 15 layers of irony " . They accuse her of " lameness " , which they attribute to spending time with Andy , and provide her with several ultimatums . She break up with them in response . Ann ( Rashida Jones ) and Mark ( Paul Schneider ) , at the same time , celebrate their first Valentine 's Day together . In an interview with the camera crew , Ann describe the relationship as " good " , but her tone of voice and body language around Mark contradict her statements . She later become jealous when Andy dedicate a song to April , even going so far as to question April about the possibility of a budding relationship between April and Andy , to which April respond impatiently .