Can you love someone and still cheat on them? A couples therapist explores why infidelity isn't always about a lack of love—and how emotional avoidance, compartmentalization, and disconnection from self can contribute to an affair. Learn what betrayal can reveal about a relationship and what it takes to begin rebuilding trust after cheating.

Why do so many successful couples feel disconnected despite spending time together? In this article, Chicago therapist Jess Benge explores how intimacy fades, why relationships drift, and three practical ways couples can reconnect through honesty, presence, and curiosity.

Should I stay in my relationship or break up? When nothing is obviously wrong but something still feels missing, deciding whether to stay or leave can be surprisingly difficult. Benge explores attraction, chemistry, emotional intimacy, and what you may be avoiding when trying to answer that question.

A thoughtful essay about modern Midwest men, emotional intimacy, masculinity, dating, and relationships. Jess Benge examines the complexities of today's men through the lens of a Chicago relationship therapist.

Why Date Night Isn't Working explores why simply spending more time together often isn't enough to strengthen a relationship. Drawing on relationship science and real-world therapy insights, Jess Benge explains how couples can move beyond routine date nights and create the kind of everyday connection that builds lasting intimacy, emotional safety, and desire.

Chicago is a city full of options. Windy City Singles often confuse possibility with fulfillment.