Is She Really Going Out with Him?

Content Warning: This section of the guide includes discussion of bullying and animal death. 

Anna awkwardly asks Michael for a date, and he accepts. At work, Jonathan says that Crispin is visiting soon, and Anna and Will’s column needs to impress him. Still hurt over him leaving her at the Hay, Anna remains cool with Will on the outside, but internally, she admits she has a “full-blown crush” on him. Ryan Stirling’s agent replies to Anna’s date request, confirming that he will meet her for a drink. 

Meanwhile, Will sends texts with flirty references to the night in the window. Will asks about her next scheduled date so he can align his focus for the column, and she tells him about the date with Ryan. Will says Ryan is reportedly not friendly, but Anna reminds him this isn’t a serious search for a partner. Will is scheduled for a date with an older woman. He glances at her pay stub and says she needs to ask for a raise. Internally, Anna can’t deny her crush but remembers that Will’s “playing the field” in his search for the right person, and she’s not sure she can handle the potential for rejection.