In the second season of With Love, Nick starts dating Ana, who is an amazing woman, but the only problem is that he is still in love with Lily. Briana Cuoco plays the role of Ana.
Nick developed feelings for Lily in the first season, but his feelings were not reciprocated. In the second season, Nick still sleeps with a lot of women, but he never dates any of them, so when he starts seeing Ana, his friends think that this relationship might be different.
A perfectly nice girl
Henry and Jorge notice that Ana, a spin instructor who works with Nick, spends a lot of nights with Nick at their shared apartment and question him about his relationship with her. Nick tells them that he is officially dating Ana, which surprises his friends because Nick has never had a girlfriend before.
Henry and Jorge approve of this relationship, as Ana gets along with them and all the people who are close to Nick. In fact, they like having her at their apartment. Even Gladys likes Ana when Nick introduces Ana to her; Ana answers all of Gladys’ weird questions without hesitation.
Ana supports Nick when he tells her that he plans on opening his own gym. She even agrees to run classes at his gym. Ana is Nick’s first official girlfriend, and she seems to be perfect for him.
Ana and Nick’s breakup
Nick likes Ana a lot but not as much as he likes Lily. He does not invite Ana to Jorge’s engagement party, even when she sends a gift. It is only when everyone around Nick tells him that he should have invited her that he realizes he did something wrong.
Furthermore, Ana catches Nick’s longing stares and notices that Nick likes Lily as more than a friend, but she dismisses the thought over and over again until she realizes that she has been right all along on Lily’s birthday.
Before going to Lily’s party, Nick and Ana go to a fortune teller, who tells Nick that he must confront the feelings that he is trying to avoid in the present to attain true love and happiness in the future. In the card about his future, Nick sees lilies.
This worries Nick, and he seeks Jorge’s help. He admits to Jorge that he has been in love with Lily for years and that he saw Lily in his future when he went to the fortune teller. Unbeknownst to Nick, Ana overhears this conversation.
Nick tries to follow Jorge’s advice and be with Ana, as he likes Ana a lot and Lily only sees him as her best friend. However, Ana refuses to be with him anymore because she does not want to be Nick’s second choice.
Nick and Ana both know that she deserves better, so Ana breaks up with him. Even after dating Ana for months, Nick fails to get over Lily. Eventually, he goes on to confess his feelings to Lily and date her.
