Dear Therapist,

My marriage ended mutually over a year ago, around the same time our youngest child left home. I’m a man in my early 50s and semi-retired—I stepped away from my previous career but am now wondering what meaningful work might lie ahead for me.

While the idea of a new chapter excites me, I feel overwhelmed by all the decisions I need to make: what I want to do, where I want to live, and who I want to share this next phase with. I’ve decided to start with the last question first, as I feel somewhat lost without an important relationship in my life. However, dating has changed so much, and my attempts so far have been unsuccessful, leaving me stuck.

Signed,
Lost

Dear Lost,

You’re navigating a tremendous amount of change all at once—it’s no wonder you feel overwhelmed. Major transitions like retirement, grown children leaving home, and becoming newly single challenge long-held roles associated with your identity, including some traditional roles of masculinity: provider, protector, procreator. It’s natural to feel unmoored and ask, “Who am I if not these things?”

Of the three big questions—work, home, and partner—you’ve chosen to focus on finding a relationship first. I’d suggest reversing that order. Instead, start with what defines you as an individual in this next phase of life. Otherwise, there’s a risk of relying on a new relationship to provide answers to questions only you can answer for yourself.

Our relationships often suffer when we look to someone else to fill an inner emptiness. This approach can lead to co-dependency, where our happiness hinges on the presence of another person. Such an imbalance places unfair expectations on both the partner and the relationship. This weight is often too heavy to sustain. A healthy and fulfilling union begins with cultivating contentment within yourself.

You mention feeling excitement about the freedom to explore this next chapter. Hold onto that. This is an incredible opportunity to rediscover aspects of yourself that may have been put on hold during earlier life stages. To help keep this perspective alive, try framing this time in a positive and empowering way:  ‘I am exploring and discovering who I am.’  ‘I am designing my second act.’  Find words that resonate and use them as a compass when feelings of doubt or anxiety arise.

It’s also worth remembering that you don’t need to have everything figured out before taking your next steps. Sometimes we stay stuck because we believe we need a detailed plan before moving forward. Instead, allow yourself to play and explore. Follow your curiosity. Whether that means trying new hobbies, volunteering, traveling, or learning a new skill, let your interests guide you without attaching pressure to the outcome. These experiences may uncover your next professional path—or they might simply bring joy and help you grow. Either way, this approach builds self-awareness and can lead to unexpected opportunities, including meaningful connections with others who share your passions.

You’re embarking on an exciting journey of self-discovery and reinvention. Trust that by focusing on yourself first, the rest—work, home, and even love—will naturally fall into place. Best of luck!

Yours,

Do you have a question for Dear Therapist? Send it to [email protected] with Dear Therapist in the subject line and Charlotte Fox Weber or Kelly Hearn will get back to you.