Conjure up a mental image of a single man in his fifties. What comes to mind? Is it an irresistible “bad boy” type who gets your juices flowing—but the fact that he has three ex-wives gives you pause? Or is your image that of a sweet, nerdy-ish widower whom you can’t decide if you should date or set up with one of your girlfriends? Or (heaven forbid) did the question trigger thoughts of your own ex?

What this exercise highlights is that men in their fifties, like men of any age, defy categorization, and this especially holds regarding what they’re looking for in a woman. Clearly, personal life experience, role models, values, and just plain character significantly impact any individual man’s relationship goals, no matter his age. That said, as a therapist—and also longtime friend of many single men in their fifties, I really do hear it all and can attest to various common desires. So based on psychological facts together with literally hundreds of hours of heartfelt male confidences, here’s how to loosely “decode” what that fifty-something-year-old man you’re dating may be all about romantically.

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Many Of The Same Things Women Want

In fact, many single men in their fifties, divorced or not, are looking for exactly the same things as you. That is, they want to find a monogamous, permanent “plus-one,” along with all the benefits that entails. Here, the term, “benefits” refers to perks like having a ready companion with whom to paint the town—and in some cases even explore the world. Interestingly, nationwide Pew polls consistently show that 76 percent of adult Americans are married or wish to be. But how do you connect with those men?


It is noteworthy that men in their fifties still have nearly twenty times the testosterone of women, which fuels sex drive, so out the gate they’ll pursue partners with whom they feel a “spark” or chemistry. (Think: sex appeal.) And, of course, sex can be a powerful part of a fulfilling relationship at any age. That said, don’t allow yourself to be intimidated or pressured into anything you aren’t comfortable with or ready for. Know that if a fifty-something-year-old man is truly into you and is looking for a serious relationship, he won’t walk if he has to wait for sex.

Honesty (And Open Communication)

One might assume that by the time a man is in his fifties, he’d have learned that lying to a partner (or a potential partner) will likely not end well, but for some men at least, that lesson has eluded them. Meaning that, yes, there are fifty-something-year-old Lotharios out there who will say anything to sleep with you.

Fake-Divorced (And Other Omissions): As illustration, my patient Natalie was highly invested in a 52-year-old corporate attorney she’d been dating for a month who led her to believe he’d been divorced for several years. He even discussed a recent breakup with a long-term girlfriend. But upon returning from a weekend trip where the couple slept together for the first time, Natalie’s partner broke a deafening car-ride silence with the bombshell that he was actually still married, but lived separately from his (conveniently) out-of-state wife! In hindsight, Natalie realized that each time she brought up the subject of family, he’d been decidedly evasive.

While Natalie’s experience is extreme, it does underline the importance of having early discussions about family, particularly exes and kids. While you don’t want to be pushy or intrusive, if you’ve been dating someone even for a short while and they always avoid discussing family, unless the topic is inordinately painful for them, the omission could be a sign that they’re hiding something. Or, more likely, they simply don’t see you in their lives for the long haul.

Confidence & Positivity

In sum, both chemistry and character matter. A lot. Meaning that somewhere in a fifty-something-year-old man’s personal history there’s probably an important woman who however outwardly attractive, eventually proved herself to be an emotionally abusive ‘B,’ as in brutal. That’s why men with more life experience are particularly drawn to partners with an especially kind, positive vibe, or what a Harvard study called, “emotional vitality: a sense of enthusiasm, of hopefulness, of engagement with life, and the ability to face life stresses with emotional balance.” Similarly, evolutionary psychology shows that women who believe they’re going to be successful with men generally are, because expectation of success drives one’s actions in a forward-moving direction likely to achieve positive results. So now is time to shore up optimism and confidence—and slash self-doubt. Not to mention honing flirting skills, arguably even more critical to early stage attraction than appearance.

About those mental images, personally, I vote for dating the sweet, nerdy guy. Just trust me on that one.

Compatibility With Family

A man in his fifties who is looking for a committed relationship is going to seek a woman who he believes will integrate well into his life, meaning she’ll get along with his friends and family. While this is less important at the beginning of dating (when a couple is mostly trying to figure out if they’re compatible), it becomes crucial as a relationship progresses, especially if there are kids involved. Even earlier on, shared or relatable “kid” experiences often bring couples closer. For instance, given that you and a dating partner are already attracted to one another, the fact that you both can commiserate over, say, your kids’ grueling college application process could very well seal the deal.

In a less fortunate scenario, down the line many women make the mistake of forcing a choice between them and their partner’s kids, especially when it comes to spending time—and, not infrequently, money. Depending on the situation, your partner’s teenaged or even adult children may at times come first. (And vice versa.) In fact, some fifty-something-year-old men confide they like to date women who are mothers themselves because they believe these women will better understand their commitment to their kids.

No Ex-Drama

Parental devotion, however, is emphatically distinguished from over-attentiveness to one’s ex, with whom you or your partner truly may need to set better boundaries or dial down the drama. For instance, some men continually prioritize their ex’s needs. One example: A patient’s boyfriend cut short a long-awaited celebratory dinner with her to help his ex with a computer issue. Another common problem is when one’s ex (either sex) harshly speaks of and/or undermines the dating partner (and often, the other parent) to the couple’s kids. Depending on how entrenched these dynamics are, professional assistance may be necessary for real change.


Given the odds that a fifty-something-year-old guy you’re seeing is separated or divorced, it’s vital to find out why. Specifically, a man who left his wife due to a mid-life crisis of sorts where he somehow realized he was no longer “happy” is generally going to be a poor dating risk. Notably, he may be unduly focused on finding an “exciting” woman as a counterpoint to his perceived experience of boredom or monotony in his prior marriage. The problem is that mid-life-crisis-guy is also likely to bolt whenever that excitement wanes with you (as it inevitably does in any long-term relationship). Not to mention that trophy wives eventually tarnish, too.

In an opposite scenario, if a fiftyish-year-old man got divorced because, for example, his wife was cheating, abusive, or she abruptly left without good reason, then he may well seek a solid relationship where loyalty and trust are key. Likewise, psychological “flexibility” (i.e. empathy and reason) are especially attractive at any age. As University of Texas at Austin psychologist, David Buss, PhD, explains, characteristics such as “fidelity, loyalty, kindness, dependability, and intelligence” are paramount to long-term mating. What’s more, those attributes take on even greater importance to anyone who has been burned by an ex, let alone an ex-spouse.

Common Interests & Similar Beliefs

Research reveals that women who are candid with men about what they want also attract men with similar goals and values. Of course that doesn’t mean bringing up marriage on a first date, but it does mean being honest with someone about what you want in life. Or even in the moment. So if he—or, more rarely, you—is mostly looking for a casual hookup or a purely physical relationship, that’s fine as long as everyone is upfront about it.

5-Day Divorce Recovery Crash Course. Take the first steps in your recovery and start healing today! Send me the free emails
5-Day Divorce Recovery Crash Course. Take the first steps in your recovery and start healing today! Send me the free emails