First Date Questions You Need To Ask When You're Over 50

It's no secret that as you get older, dating seems to gets harder. And putting yourself out there over 50 can feel like an particularly daunting task. "Mature individuals have an established design. They already have a home, family, and friendships that add to their wellbeing," Susan Winter, bestselling author and relationship expert, exclusively told us. "Mature daters have their own emotional baggage and relationship expectations to contend with when they meet someone new," she added, noting many singles in their 50s and beyond are less open to compromising for romance (and that's not necessarily a bad thing).

But there are ways to make stepping out for a first date as a mature person a little easier, and it involves asking the right questions early to ensure you're compatible. If the signs "The Golden Bachelor" star Gerry Turner and Theresa Nist's relationship wouldn't last taught us anything, it's that you don't want to get engaged only to find there's no compromise on where you'll live. So we asked Winter to break down the best first date questions and why they're so important.

Asking someone if they're single may seem redundant on a first date (no matter how unconventional it is), but it's one of the most important times to ask. According to 2021 data from the United States Census Bureau, 90% of adults 60 or older have been married at least once, so there's a chance your date could be dealing with a separation or divorce. Equally, if you're going through a split, it offers you the opportunity to address it in a natural way. "Prequalify that your partner is free and clear of any entanglements. This means less drama for you to contend with," Susan Winter said.

Of course, there are situations where someone yet to finalize their divorce is over their ex and in a healthy place to date again. But it's important to make that distinction before you become too involved by politely enquiring about their past relationship. "[Ask] 'If it could have worked out, would you have wanted it to work out?' Perhaps the divorce wasn't their idea and they still holding a torch for their former spouse. You don't want that," Winter said. There's isn't one size fits all advice for how long someone should wait to date after a serious relationship, but MentalHealth.com recommends taking one month out of the dating game for each year of the relationship.

Asking someone to describe their ideal partnership on a first date will help you find out early if you're compatible in a practical way. "This reveals their expectations for you. What if they say a great mate is one who enjoys cooking and staying at home, but you're a driven professional that seeks relaxed companionship at the end of the day?" Susan Winter asked. It's easy to get swept up in the idea of someone over the practicality of your romance, but this question will help you avoid that.

This prompt will also ensure you both have realistic expectations about each another's lifestyles, as people 50 or older may not be open to changing their routine for a new partner. "Do they want to go hiking with you on the weekends or play golf with their buddies? Do they like to travel? Do they have a growth mindset? You want to get an idea of what you're walking into," Winter said. Though it's okay not to love all of your partners hobbies, it's important to have a few things in common.

Asking your date if they'd be willing to relocate is particularly important if you wouldn't consider moving. If you have strong roots (such as family, friends, or business ties) and wouldn't leave your local area under any circumstance, finding out early on if they feel the same will avoid heartache down the line. "People in their 50s know what they like, what they don't like, and what they won't tolerate. There's less willingness to bend, amend, or give up something they want just for the promise of love," Susan Winter told us. "They're less inclined to take risks that involve relocating to a new city or making a dramatic lifestyle change," she added. A 2019 HireAHelper survey found only 12% of people aged 54 and up had moved for a relationship, much lower than the 31% of people aged 25 to 34 who upped sticks for their partner.

Even if you both live in the same city, it's never a bad idea to know early on if someone has an open mind about moving. Work or family commitments requiring relocation could happen at any time and asking this question early on will set both of your expectations.

Though many people may think they're open to falling in love and starting a committed relationship, sometimes, until you ask the question directly, even they may not know where they truly stand. And you don't want to be playing guessing games as a mature person. "Wanting love and really being open to it are two different things ... This might seem unnecessary or intrusive, but it's a very important question," Susan Winter told us. "Your best shot at meaningful partnership is to find the person who's 'locked and loaded' — ready, willing, and able to be in a committed relationship," she added.

Knowing in no uncertain terms where your date stands will make deciding to see them again, or not, a lot easier. "Every date is 'dating for data.' You are looking for information about what you like, what you want, and what feels good and comfortable for you," Winter explained.

Of course, you may not be looking for a committed relationship yourself, and that's totally fine. They may get a bad rep, but situationships aren't all bad. If that's what you're hoping for, this question allows you to share that with your date (because communication is always key). You may even find they want the same thing, as a 2022 Pew Research Center survey found 36% of Americans on dating apps aged 50 or older were looking to date casually.

Asking someone what matters to them can elicit several different personal responses and will give you a good idea of what they truly hold dear. If your date mentions children or grandchildren, you'll know they're more family oriented. If they discuss their hobbies, that says a lot about how they value their spare time, allowing you to think about how those passions fit with your own.

No matter if you get the response you were hoping for or not, asking this question can tell you a lot about their priorities. "You hope for the best, but at the worst, discover something new," Susan Winter said. "The person you're meeting may be a dud, or they might have something of interest to share. And if you find them interesting, you may want a second date." If they don't meet your expectations though or you lack compatibility, it's better to confidently dish out rejection and let them know you're not interested sooner rather than later.