Dating at Midlife

A Road Map for Newly Single Clients

Magazine Issue
May/June 2020
A middle-aged man and women clink wine glasses


Q: I’m seeing more and more clients who want to date again after a divorce in midlife. Like them, I’ve been out of the dating scene for decades. How can I help them?

A: It’s understandable how our once-married clients who find themselves single again in midlife might feel a bit like Rip Van Winkle—as if they’d fallen asleep only to wake up in a wildly different time and place. Navigating the brave new world of online dating is challenging enough, but what can be harder is tolerating the risk of opening up again, particularly given the fast-paced way relationships tend to start and end these days.

My 46-year-old client Layla came to therapy several months after her divorce. She was proud of how she and her ex-husband had ended their marriage and were coparenting their teenage sons, but she felt ambivalent about the idea of dating again. She’d downloaded a dating app but was too nervous to create a profile. The prospect seemed exhilarating, utterly frightening, and entirely disorienting, all at the same time. In sessions, she’d talk about her longing for connection, companionship, and touch, but then she’d quickly move into a self-critical stance, saying things like, “That sounds too needy; I should be able to stand on my own two feet,” or “I need to just focus on my kids and my job.”

My work with Layla centered on helping her expand relational self-awareness, which I define as an ongoing curious and compassionate relationship with oneself. It’s about understanding one’s relationship to relationships. Why is that important in the dating world? It becomes the foundation for relational choices that feel aligned and enlivening, rather than anxiety invoking and overwhelming. Here are the top five ways I help my single-again clients build relational self-awareness.

Integrating a Breakup Story

Like the adage that you are what you eat, I tell my clients that they are the stories they tell about their lives. When it comes to the painful chapters in our lives, many of us protect ourselves by telling thin, linear, and unprocessed stories. That’s why narrative therapists Gene Combs and Jill Freedman talk about helping clients “thicken their narrative.”

Thickening and integrating a breakup story is especially important as people begin to date again. When their story lacks relational self-awareness, they tend to be guided solely by one desire: to choose someone who is “not my ex,” which often leaves them reactive and overwhelmed the moment anything in the new relationship even vaguely resembles something from the old one. Alternatively, a relationally self-aware story about the old relationship is empowering. When clients make peace with the fact that they’ll “take themselves with them” into their next relationship, what happens with their new dating partner becomes something to be curious about, rather than a potential source of red flags to run from.

Layla had been so focused on how her sons were being affected by the end of their parents’ marriage that her own relationship story hadn’t developed beyond “we grew apart.” In our work together, I listened for what was being left out of her narrative—her loneliness, her passivity, the parallels between the patterns in her marriage and those from her family of origin. Through these conversations, her story began to shift from “we grew apart” to something with much more depth and nuance.

Choosing Love over Fear

It’s important to help our single-again clients get clear on their motivations for dating. When you boil it down, there are really only two kinds of energy that drive us in this arena: fear and love. The energy of fear is about passivity, scarcity, and avoiding something worse. The energy of love is about choice, agency, and resilience. When fear is the prime motivator, the narrative sounds something like, “I have to find someone before my ex does,” or “I’m terrified to be alone,” or “I don’t have a choice.”

When love is the prime motivator, however, the narrative sounds something like, “I value connection and intimacy,” or “I’m excited about what I bring to the table,” or even “I’m apprehensive, but I trust myself.” We can’t expect our clients to be in a mind frame of 100 percent love and zero percent fear, but when we invite them to name how the mix of love and fear are living inside of them, we expand their relational self-awareness.

I often ask clients nervous about dating again, “What would you do if you weren’t afraid?” This question puts a bit of space between themselves and their fears, invites them to imagine new possibilities for this chapter of their lives, and helps them begin to get excited about that potential first kiss or about falling in love.

Although dating at midlife can feel like a brand-new endeavor, plenty of past experiences offer guidance. I have two exercises I recommend. The first is to recall dating before marriage. They may never have “swiped right,” but they probably sat across from a stranger and explored the potential for connection. The second is to ask clients about other times a stranger has turned into a friend, socially or even at work. By remembering these experiences of building a connection over time, clients can feel less afraid and more grounded as they navigate the uncertainty of dating.

Considering the Stakeholders

As a systemically trained therapist, I’m always thinking about my client’s extended social network—the people who may not be in the therapy room but who are stakeholders, allies, or roadblocks nonetheless. Single-again clients often have a chorus of well-meaning friends and family members chiming in with advice and directives. Layla, for example, was exhausted by her mother’s incessant questioning about whether there was “a new man” in her life yet. She was just as overwhelmed by the single women in her life telling her there were no more “good men.”

Together, we practiced putting some breathing room between her and her squad, so that she could start listening from within and centering on her own truths, perceptions, and desires. One simple but helpful practice was for her to come home after a date and spend some time “solo savoring,” which meant reflecting and journaling about her experience on the date before debriefing with her best friend. She also let her best friend know that in these debriefs, because she values her opinion and listens to it so closely, it would be great if she could set her intention to help Layla hear herself more clearly.

The children of our dating-again clients can be key stakeholders. Dating parents certainly need healthy boundaries to protect their children’s well-being, but clinicians must discern the degree to which clients’ fears about how their choices may affect their children are holding them back. Layla found that as soon as she sat down across from a man on a first date, she immediately began to imagine how he’d interact with her kids. It was distracting and got in the way of her ability to access the erotic and romantic side of herself. We worked on holding two truths at once: it’s vital that whatever partner she ends up with gets along with her children and intimate relationships take time to build. So trying to imagine a man she didn’t know with her children was premature and fruitless, mainly because she’d never introduce a stranger to her children.

In these first-date moments, Layla had to try her best to stay in the moment while understanding that she had to give herself time to get to know him, recognizing that the more she got to know him, the easier it would be to imagine a future—or know for sure that there wouldn’t be one. Ultimately, I invited Layla to give herself permission to notice and honor the pulls of attraction and curiosity, trusting them to exist alongside her responsibilities to her family. She got better at this by practicing mindfulness skills, noticing without judgment when her mind would fast-forward to family introductions or future vacations and gently bringing herself back to the moment.

Examining Gender Expectations

Gender-role expectations can play out most powerfully in the realm of intimate relationships, where the sexual script tends to equate masculinity with pursuit and femininity with passivity. With LGBTQ+ clients, too, this template can shape how much people feel they have permission to initiate versus hang back in the early stages of relationships. But feeling like a predetermined role requires you to wait and remain silent about what you want (clarification of relational boundaries, for example) is a setup for feeling resentful and disempowered.

With Layla, I’d listen for ways in which this predominant sexual script was shaping her experiences with online dating. For example, she’d matched with a guy who seemed interesting and interested. After messaging back and forth for a week or so, she’d become discouraged that he wasn’t proposing a next step, like a phone call or a date. Simply validating her frustration would subtly reinforce the idea that her only move was patience. Instead, I empathized with her feelings while inviting her to consider what might be keeping her from proposing a next step.

Of course, this narrow script can be constricting for both genders. Men who date women may feel burned out by how much they need to initiate in order to stay engaged with a potential partner, and women are often burned out by the cascade of queries they feel obligated to respond to. But there’s a dating app designed to fix that! On Bumble, created in 2014, a heterosexual woman can’t connect with a man until she initiates contact with him first. In same-sex matches, either partner can initiate contact.

Defining Boundaries and Safety Precautions

According to the National Sexual Violence Resource Center, one in three women and one in six men are survivors of sexual violence, so safety is a big concern for people in the dating world, especially women who date men. Therapists can help clients remember that while most people are well-intentioned and nonviolent, taking dating precautions is important. Here are a few basic ones: meet at a public location instead of being picked up at home; get a Google phone number for dating, rather than giving out your cell; tell someone close to you where you’re going; limit the number of drinks you have on a date and get them directly from the bartender; and don’t accept a ride home. When working with men, it’s important to help them honor women’s safety concerns as understandable and smart, rather than viewing them as a personal affront. In fact, men can be allies by implementing principles like these right off the bat.

It’s also important to talk to clients about their sexual boundaries. Rather than focusing on sexual strategies to get someone interested in them (the unfortunate focus of many dating books), they can work on living the values they’re seeking in a partner and seeking partners who have similar views on relationships. Externally dictated parameters—like the “third-date rule” (don’t have sex until the third date) or the “sexclusivity rule” (don’t have sex until you’ve defined yourselves as a couple)—may feel comforting to people struggling to navigate the dating world, but we can help them proceed less rigidly by expanding their relational perspective with questions like: How might you know when you’re ready for sex? What would you be thinking, feeling, doing? What are you seeking or longing for in sex? Who were you sexually in your marriage? Who might you want to become sexually now? What parts of your sexual self have been neglected and need reclamation?

We’ve all been trained to be aware of countertransference issues with clients, but when working with the single-again population, we need to attend to the understandable pull of voyeurism. After all, entire media empires are built upon the excitement of watching people date. While the interesting ups and downs of dating life will inevitably play a part in therapy, it’s important that we don’t let sessions turn into episodes of The Bachelor or 90-Day Fiancé.

We have to watch out that our desire to see our clients find love doesn’t push them in the wrong direction, and that our impulse to help them establish boundaries doesn’t impose our own rules and truths. Dating will always be a fraught endeavor, and ultimately clients will need to rely on their own inner fortitude and wisdom to guide them.

Even during a global pandemic, when the option of face-to-face dating has been mostly taken off the table, we can help our clients tap into that inner wisdom. Some people are pressing pause on their quest for love, opting instead to invest their energies in relationships with family members, friends, and, of course, themselves. Others are continuing to swipe right, moving from messaging to video chats to video first dates. But no matter what the dating landscape looks like—online or in person—relational self-awareness can guide us through it.


iStock/Dean Mitchell

Alexandra Solomon

Alexandra H. Solomon, PhD, is internationally recognized as one of today’s most trusted voices in the world of relationships, and her framework of Relational Self-Awareness has reached millions of people around the globe. A couples therapist, speaker, author, professor, podcast host, retreat leader, and media personality, Dr. Solomon is passionate about translating cutting-edge research and clinical wisdom into practical tools people can use to bring awareness, curiosity, and authenticity to their relationships. She is a clinician educator and a frequent contributor to academic journals and research, and she translates her academic and therapeutic experience to the public through her popular and vibrant Instagram page, which has garnered over 200K followers. She is on faculty in the School of Education and Social Policy at Northwestern University and is a licensed clinical psychologist at The Family Institute at Northwestern University. Her hit podcast, Reimagining Love, has reached listeners across the globe and features high-profile guests from the worlds of therapy, academia, and pop culture. She is the award-winning author of two books: Taking Sexy Back: How to Own Your Sexuality and Create the Relationships You Want and Loving Bravely: 20 Lessons of Self-Discovery to Help You Get the Love You Want which was featured on the TODAY show. You can visit her online at and on Instagram at @dr.alexandra.solomon.