Hi, it’s Wednesday, and that means it’s time for another video edition of Widower Wednesday. I’m Abel Keogh, author of the book Dating a Widower. Today, we’re answering a question about large age gaps in relationships. This comes from a viewer who wrote: “There is an 18-year age gap between me and my widower. I’m 45, and he is 63. What challenges should we think about as we move forward, and from your coaching sessions, do these relationships have a chance of working out?” These are great questions, and I’m glad you’re thinking ahead about some of the age-related issues you might experience in addition to the widower-related ones.
If you want these relationships to work, you need to consider the long-term implications of being with someone with a 20-year age gap before committing. Every relationship is different, but I think there are five key factors to consider. The first is different life stages and long-term compatibility. At 45 and 63, you’re likely in different life stages. You might have years of career growth, travel adventures, or minor kids still living at home, while he may be thinking about retirement, slowing down, or even health concerns. Ask yourself: Do your long-term goals align? Are you okay with the possibility of becoming a caregiver sooner rather than later? As the age gap stretches into the 70s and 80s, health concerns often become more prominent. How do you both envision the next 10 to 20 years? What is your life like now, and do you see that aligning?
The second factor is energy levels, activities, and lifestyle. What are your energy level and lifestyle like right now? Does he match it? In your 40s and his 60s, he might be able to keep up, but what about in the next 10 to 20 years? What do you both enjoy doing in your free time, and can you continue doing those things as he gets older? The age gap will become more noticeable, especially when it comes to energy levels and interests. Are you going to be satisfied if his energy decreases or if his physical or mental abilities decline, limiting the activities you enjoy now? These differences don’t have to be deal-breakers, but you need to acknowledge and think about them.
The third factor is work, retirement, and finances. At 63, I assume he’s nearing or already in retirement. What’s his financial situation? Is he financially independent? What’s his retirement income like? Are there expectations that you’ll contribute more as he ages, especially if you’re still working while he’s retired? How does that dynamic affect your lifestyle if he’s at home all day and you’re working a 9-to-5 job? You need to have conversations about money, estate planning, and long-term financial security. Since he’s likely to pass away before you, what are the plans? Does he have kids, and how does that factor in? Every situation is individual, but these are things to consider.
The fourth factor is intimacy and physical changes. A 20-year age difference means physical aging will impact the relationship, especially as he gets older. Health issues, sexual function changes, and shifts in energy levels can all affect intimacy. Is he open to discussing these things? What are you willing to accept or not accept? Is physical connection an important part of your relationship? Consider how these factors might evolve not just in the next one, two, or three years, but 5 to 10 years down the road.
The fifth and biggest factor is end-of-life considerations. This isn’t the most romantic topic, but it’s an important one. If you’re committing your long-term future to someone 20 years older, you have to face the reality that he’s likely to die before you. You could be widowed in your 50s or 60s. There’s nothing wrong with that, but it’s a reality compared to a relationship with someone your own age. Are you prepared emotionally and practically for the possibility of becoming widowed or a long-term caregiver? What are his wishes regarding living arrangements and long-term care? There’s no right or wrong answer, but are you thinking through the worst-case scenario? Are you okay with it? Is he okay with it? Are you on the same page?
Now, your real question is: What are the odds of this relationship working out? The answer is yes, it can work. What matters isn’t the age gap itself but how well you navigate the challenges it brings. If you can both communicate about these issues, respect each other’s life experiences and differences, and have common ground on the things that matter most, the relationship has a strong foundation. But if you find yourself making too many compromises or ignoring red flags, it’s worth reevaluating whether this will truly bring you long-term happiness, especially 10 to 20 years ahead.
Instead of asking, “Can this work?” ask yourself, “Is this the life I want?” If you’re comfortable with the realities of dating someone nearly 20 years older and see a future that excites you, then age is just a number. But if these differences feel like obstacles rather than adjustments, it’s okay to acknowledge that love alone isn’t enough to make a relationship sustainable. In the relationships I’ve seen that work, they have a long-term view and are aligned on it. They’re okay with the possible challenges. If you’re in your 50s and he’s in his 70s, are you okay with being a long-term caregiver? If you’re widowed in your 60s, are you prepared for that? If you can take that long-term view and agree this is the life you want for the next 10, 20, or 25 years, then go for it. If not, be honest with yourself—maybe the age gap is too much to overcome.
I’m Abel Keogh, author of the book Dating a Widower. Leave your stories and comments about large age gaps below, and I’ll see you all next Wednesday.
