Rachel recently discovered that her fiancé has been secretly paying his ex-girlfriend Vanessa’s rent from their joint account for almost a year. He says Vanessa fell on hard times after losing her job and swears there’s nothing inappropriate going on between them. According to him, he only kept it from Rachel because he knew she wouldn’t understand. But for Rachel, the betrayal runs deeper than the secrecy and the shared money being spent on another woman: they’re supposed to be saving for their wedding.Her fiancé argues that Vanessa has no one else to turn to, and that helping her is a reflection of his character. But is this generosity or a major breach of trust?

How should Rachel handle what feels like extreme financial infidelity and the fact that her fiancé is framing it as moral high ground? Could this “charity” spill into other parts of their relationship? Is Rachel being too harsh, or just setting reasonable boundaries? Sarah, Ellen, and Ryan weigh in to help Rachel make sense of this complicated situation.

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Amanda and her husband, Tyler, both work for the same company. After Amanda is promoted, she suddenly finds herself in the uncomfortable position of managing her own spouse. While Tyler was initially supportive, his behavior has shifted: he’s now distant at work and at home, where frequent arguments often spiral into clashes over what he sees as a lack of respect for him as a man. At the same time, one of Amanda’s employees, Brandon, has been consistently encouraging and supportive, and she finds herself increasingly drawn to his company. Feeling caught between her husband’s growing resentment and her own complicated emotions, Amanda turns to Sarah for guidance on how to navigate her marriage, her role as a boss, and her emerging attraction to Brandon.

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Trina’s best friend, Misty, has broken one of the biggest unspoken rules in the friendship handbook: she’s dating Trina’s long-term ex-boyfriend, Brandon. Even though Trina was the one who ended the relationship and things ended amicably, it still hurts. Misty was there for all the post-breakup drinks and ugly cries, but when Trina confronted her, Misty stood her ground, saying that Trina was the one who dumped him and Brandon is fair game now. Even Trina’s mom thinks she needs to let it go or risk losing both of them. Should Misty have told Trina about her feelings first? And is Trina justified in feeling hurt and uncomfortable?

In our second session, Aaron, 28, has fallen hard for Abby, 50. She’s brilliant, independent, adventurous and unlike anyone he’s ever met before. After nine months of dates that felt straight out of a movie, Abby ended things. She doesn’t see a future and doesn’t want to invest more time in something she believes won’t last. She wants Aaron to find someone closer to his own age, but Aaron doesn’t want anyone else. He wants Abby. Should he respect her decision and walk away or fight for the relationship?

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