Lisa O
Dating after 50 can be incredibly fulfilling, but it also comes with a different set of expectations. You’re both grown adults, likely with full lives, histories, and hard-earned perspectives. That’s why certain questions, even if well-meaning, can strike the wrong chord. If you want to build a connection based on mutual respect and authenticity, here are 15 questions to avoid when dating a man over 50, and what to focus on instead.
“Why didn’t your last marriage work?”
While curiosity is natural, this question dives into deeply personal and possibly painful territory. Many men over 50 have gone through significant relationships—some ending in divorce, others through loss. Asking this too soon can feel like poking around in a wound that may still be healing. Even if you’re hoping to understand what went wrong to gauge compatibility, it’s better to wait until trust has been established.
“Are you looking for someone to take care of you?”
This question can feel belittling, even if you intend it as playful or lighthearted. Many men over 50 are fiercely independent and proud of the lives they’ve built. Suggesting they might be seeking a caregiver or someone to pick up after them can be perceived as offensive, not humorous. It may also hit a nerve if they’ve had health issues or previously been in caretaking relationships.
“How much money do you have saved for retirement?”
Financial compatibility is important, but diving into someone’s retirement savings or assets too early can feel invasive. At 50 and beyond, people may have complex financial histories: ex-spouses, dependents, debt, or significant wealth. Asking this question too soon can give the impression that you’re more interested in financial security than in who he is. It also pressures him to disclose private matters before emotional trust is established.
“How old are you, really?”
By the time you’re both over 50, age should be the least of your worries. This question, even if asked jokingly, can come off as distrustful or rude. It implies you think he’s lying or that his age might be a dealbreaker. Most people over 50 are proud of their age, or at the very least, accepting of it. They’ve lived, learned, and grown through decades. If he’s been upfront with you, there’s no need to press the issue.
“Do you still go on dates?”
This may seem like a light question, but it can unintentionally sound like you’re questioning his social life or assuming he’s out of touch. Many men over 50 are active, socially engaged, and open to new experiences. Instead of framing it as a curiosity about his habits, talk about how you both enjoy spending your free time or what kind of outings bring joy.
“Are all your parts still working?”
This may be intended as a cheeky comment, but it risks crossing into hurtful territory. Health and bodily changes are sensitive topics, especially for men who may already feel pressure to maintain strength, stamina, or vitality. Asking about “working parts” feels clinical and dismissive, and may provoke shame or discomfort. If physical compatibility is important to you, approach it with maturity and empathy, not sarcasm.
“How much alimony do you pay?”
This question touches on finances, legal obligations, and ex-relationships all at once, making it a perfect storm of discomfort. Even if you’re asking out of curiosity, it can sound like you’re measuring his baggage or financial availability. Many men over 50 have financial ties to their past, whether through alimony, child support, or shared investments. Those are private details best left alone until your relationship warrants such conversations.
“Do your adult kids like me?”
If you’ve only just started dating, this question puts unfair pressure on everyone involved. Relationships with adult children can be deeply nuanced—ranging from extremely close to strained or distant. Expecting instant approval or involvement isn’t realistic. This question can also make him feel like he needs to “sell” you to his family or manage their reactions. Let relationships with his children develop at their own pace.
“Are you dating anyone else?”
Wanting exclusivity is valid, but asking this question too early can feel possessive. At this stage in life, many people are cautious and date slowly. Some explore options before committing. Rather than issuing a demand or fishing for reassurance, share your own intentions first. Say something like, “I’m enjoying getting to know you and focusing on one person feels right to me.”
“Would you be willing to relocate for love?”
Relocation is a major life decision, especially for people in their 50s who may be tied to family, work, or community. Asking this question early can feel overwhelming and unrealistic. It might come across as if you’re already planning a shared future when the foundation hasn’t even been built. While it’s okay to wonder about long-term compatibility, focus instead on learning about his current life.
“Are you over your ex-wife yet?”
This question, though direct, can sting. Even if he’s long divorced, emotional closure isn’t always black and white. He may have complicated feelings—grief, regret, or even indifference—but asking this forces him to prove emotional readiness on the spot. A better approach is to observe. Does he speak about his ex with bitterness, nostalgia, or respect? His behavior will tell you more than his words. If he seems emotionally available and present with you, that’s what matters.
“Do you have any medical issues I should know about?”
Health concerns are common as we age, but this question requires sensitivity and timing. Men may not feel comfortable sharing personal health details unless they truly trust you. Asking too early can make them feel vulnerable or exposed. Instead, build an environment where honest conversations feel safe. Share your own health routines or challenges. Ask broader questions about wellness, habits, or energy levels.
“Do you still want more kids?”
This is a loaded question for someone over 50. He may already have grown children, be a grandfather, or feel completely finished with parenting. On the other hand, he may still be open, especially if he hasn’t had children yet. But phrasing it like this puts pressure on him to respond to your hopes, not his own desires. If children are part of your future vision, speak from that place: “I’ve always wanted to be a mom again—how do you feel about parenting at this stage of life?” This opens the door without making assumptions or demands.
“Do you think we’re moving too slow?”
By the time you’re dating in your 50s, you realize real connection doesn’t run on a clock. Rushing to define the pace often stems from anxiety or a desire for control. But pressure can make a man shut down, especially if he’s taking his time intentionally. Many people over 50 have experienced heartbreak, and they move with caution—not indifference. Instead of asking this question, reflect on whether your needs are being met.
“Would you cry if I died?”
This kind of hypothetical sounds poetic on the surface but carries emotional manipulation underneath. It’s a dramatic test of affection that rarely gives you the answer you’re truly looking for. Worse, it can confuse or even disturb your partner. People show love through action, reliability, care, and presence, and not through imagined grief. If you’re feeling uncertain about how much he cares, talk about your needs more directly.