Unpopular Opinion: Men Over 50 Deserve a 2nd Chance
October 9, 2025
I don’t mean get back together with the man you divorced.
I certainly don’t mean stay with someone who abuses you.
I mean, in early dating—even in texting. I mean, when something rubs you the wrong way and you’re ready to call it quits before chemistry has had a chance to develop.
For every time it is wise to turn and run from someone who shows you a "deal breaker" early on, there is an example of a lasting, healthy relationship that began with some confusion and doubt. As a coach, I help women over 50 discern which scenario it is, each time. Sometimes it's right to move on almost immediately, and sometimes a man deserves a second chance.
Here are 4 scenarios that should give you pause. If you encounter them in early dating, take a beat and really consider whether or not you know enough to be sure the man is wrong for you.
Scenario 1: They Mess Up Once
Maybe he doesn’t text back right away. Maybe he cancels your first date or shows up late. Maybe his “good morning” text feels like the bare minimum when you want fireworks.
Your instinct might be to call it. Done. Out. Because you want to feel pursued and desired, like all the gurus say you should, and you can’t stand the momentary sting of not feeling like a priority. So, you protect yourself by rejecting him early.
But here’s what might really be happening: he’s overly busy. His work is overwhelming. He’s caring for an aging parent. He has ADHD and truly struggles with time management.
Or yes, he may be figuring out who he prefers among the other women he’s dating and hasn’t chosen who to focus on yet. None of these means he won’t rise to the occasion and be a suitable companion for you. Many successful relationships start out a little confusing or rocky.
I admit when I first met my husband, he was in another relationship. I didn't know it at the time, but he did! In retrospect, his lack of pursuing me made total sense. It took around 2 weeks to get it all sorted out and to be together in a meaningful (kosher) way, but I was willing to wait, in uncertainty, because I knew he was right for me.
Maybe the guy you just met really is busy or otherwise entangled. I know the current influencers are strong on urging you to wait to feel completely pursued and desired, but that's not always easy for a man to do, right away. He might flub up, especially before he knows what you like and what you want in terms of attention and affection.
One "mistake" doesn’t define an entire person. How he recovers from the mistake—how he shows up on the second date, how he communicates after a missed text—that’s the bigger deal. If you shut it down too quickly, you may never see the full story unfold.
Scenario 2: You’re Not Initially Attracted
Attraction is powerful—but it’s also tricky. So many women over 50 tell me they only want to date men who fit their “type.” Tall. Stylish. A certain level of fitness. The spark has to be there immediately, or forget it.
But what if your type hasn’t actually been serving you? What if the guys who give you butterflies are also the ones who ghost you or repeat the same patterns of your past relationships?
It can take time to rewire attraction. You may not swoon on the first date, but you might notice kindness in how he treats the waiter. Or how he remembers something small you said. Sometimes attraction sneaks up on you in the form of safety, humor, or consistent attention. Those qualities don’t always scream at you in the beginning, but they build real desire over time.
This is why I encourage giving at least a second chance at attraction. If the first date doesn’t knock you over, but you feel curious, try a second date, try a kiss, try some honest communication (which often builds attraction for women). True chemistry can reveal itself over time. Many, many people in happy relationships report that they were not initially attracted, me included.
Scenario 3: They Don’t Like the Same Things or Their Politics Differ
You see that he’s into golf, and you can’t imagine spending Saturdays watching someone hit balls across a field. Or you find out he leans differently than you politically, and you instantly picture endless arguments at holiday dinners.
What might really be happening: people tend to oversimplify or exaggerate in early dating. Nerves make us sound more rigid than we are. He may say he “loves golf,” when really he plays a few times a year. Or he may spout off about politics because he’s unsure what else to talk about, not because he insists you agree with him or isn't open to change himself.
Identical interests or belief systems are not a sign of true compatibility. You've spent years doing your interests with friends or alone, and so has he. You only need a little overlap in a few interests to enjoy time together. You don't need to agree on politics or religion, but you both have to be open enough to hear and respect each other's views.
So: Ask him why golf matters to him. Tell him why your beliefs matter to you. Going deeper into the “why” creates the genuine connection that will outlast hobbies and overcome even political differences.
Differences sometimes are dealbreakers, but sometimes they can instead be chances to grow. Couples who make it long term aren’t "same same"—they’re people who respect and adapt to each other. Before writing someone off, see what curiosity and flexibility yield.
Scenario 4: They Don’t Live Nearby
Why do the guys always seem healthier and cuter when you're visiting some other city? Of course, it makes sense that you are afraid to fall for someone who is geographically incompatible.
I understand that when you find out he lives two hours away—or worse, across the country—you immediately think: impossible.
But here’s what I know from coaching people for over 20 years: people move for love all the time. People commute for jobs, uproot for family, or split time between cities. If someone is the right match, geography is a logic problem not a deal breaker.
Of course, not everyone wants long distance, and that’s fair. But at least consider whether it’s really the distance—or your fear of investing—that’s making you say no. After all, you have lived fully without him all this time and you are fine. A second chance might look like one more phone call, an in-person meeting to really check chemistry, or exploring what geographical compromise could look like.
Romance after 50 doesn’t always follow a neat, orderly script. Sometimes you have to give life the chance to surprise you—even if it comes with a different zip code.
✨ Coaching: If you’re struggling to sort “second chance worthy” from “deal breaker territory,” that’s where I come in. Join my free webinar to learn how to date after 50 with hope, clarity, and true open-mindedness.
FAQs About Giving Men a Second Chance
1. Isn’t giving a second chance just lowering my standards?
Not if you stay rooted in your deal breakers. Abuse, dishonesty, and disrespect are never acceptable. But flaking once or not being your “type” on paper? That’s not about standards—that’s about preference and flexibility.
2. How many chances are too many?
Two or three is reasonable in early dating. After that, you’ll see a pattern. If someone keeps repeating the same issue, believe that their actions are showing you who they are. People can change, but only if they know what you want and they really want to change to be that. Both of those need to be in place, or else you're living in a pipedream to expect a new kind of behavior.
3. What if I give a second chance and feel nothing new?
Then you tried—and now you know. You don’t owe endless dates. But sometimes you need a few dates to get clarity.
4. Should I tell him I’m giving him a second chance?
Not in those words, but you absolutely must, in a kind way, say the thing that did not work for you and what you wish had happened instead. Men need clear instructions and to see a path to a win. If the second date goes better now that he knows what you want, great. If not, you can walk away without drama.
5. Isn’t life too short to waste time?
Life is too short to waste time, but it’s also too short to miss out on a potential soulmate because you were overly quick to judge. The trick is balance: stay open, but also stay discerning.
Love,
Love,
