Dating Over 50: How to Ask the RIGHT First Date Questions to Best Get to Know Someone!

What are the right questions to ask on a first date to best get to know someone? Great question! Asking the right questions is vital to revealing what you really want to know about your date. Today, Dating and Relationship Coach April Beyer offers tips and advice on how and why to ask specific questions on a first date to best get to know someone without making it feel like you’re conducting an interview. Great conversation starters on a first date!


April Beyer is the founder and CEO of LEVEL™, a hybrid of intuitive AI matching technology combined with human support to make dating effortless and rewarding again. A pioneer and 20-year veteran in the personal matchmaking industry, April has been one of the most sought after dating experts. Dr. Phil calls her “The Best of the Best” and she’s been featured on 20/20, Dateline, ABC News, morning shows, and countless other print and digital publications.


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[theredpilllion]

When I was at the gym, I asked the trainer, “What is the best machine to use if I want to attract a women?” He pointed to the ATM.

[eddy]

Something I had to learn with online dating, reveal very little personal stuff on the first date, keep the mystery going. I had a first date where the lady started making notes on the restaurant napkin!! My fault for not slowing her down and deferring her questions to another time.

These days, I go on the first date to have fun and meet someone new and not worry where this encounter may lead in the have fun. April had some good points, but really too complicated...keep it simple and have a fun date.

[anxen]

They: who do you enjoy spending time with?
Me: my cat
They: 🏃‍♂️ 🏃‍♀️

[pdxjeff]

Thank you sharing, good stuff. Never felt more unqualified to date anyone as a introvert not needing a list of friends for life to prove I’m capable of having relationships. oh well…lol

[NASAA]

For myself as an 80+ widower who has recently managed to end 8+ years of grieving, I found this an especially helpful session. The suggested questions are helping me to loosen up and evaluate myself, on the way to considering what to say to others. But there is less peer pressure at this age, after all!

[richarde]

For many people over 50, a high percentage have been in marriages that lasted many years and have been out of the dating scene for a long time (well, at least they should have been not dating). It’s like anything else - practice makes perfect. So, when meeting someone on a first date and your date seems awkward or stiff, be a little patient and understanding and try to understand from where they are coming. I find a good topic is asking about how they are finding dates, if they are finding quality dates, etc. - it helps me understand how they are approaching the dating scene and explain any stiffness or awkwardness in their presentation.

Similar to what April said, talking about the good dates she’s met, and asking why and what she found good about them, also helps me understand what she likes and if the type of guy she likes aligns with who I am.

[ronmance]

Dating is really complicated after 50, there are so many variables to consider, I think it's easier to just be friends with all your acquaintances and wait for that love bug to bite you 😉

[joes]

In my opinion don't try to get too much information on the first date people are not encyclopedias

[lifetobelived]

Since I've been in social isolation quite a bit over the last 1 1/2 years my friendships aren't as close as they used to be and some of my friends of 20 years don't align with my values any more, . I'll probably be finding new friends next year when I socialize more. The longevity of friendships wouldn't be a good evaluation of my ability to keep deep relationships.

[PorcelainLeigh]

Talking about past relationships on a 1st date?
This is NOT the time for this conversation.
If your date does nothing but talk about their ex?
They're clearly not over it, and shouldn't be dating,

[patric]

I disagree abt asking deep questions on a first meeting. I don't like discussing my previous relationship with someone I've just met. I have a process to dating. Since nowadays we're all doing the online dating thing, I have 3 screening questions to even continue chatting. If we are compatible then I chat for 1 or 2 wks and I observe their behavior and answers, if they don't show interest or don't ask to meet in person I move on. This prevents me from meeting energy vampires🙂

[packrcch]

don’t ask a question that you are not comfortable answering about yourself.
don’t obviously play peek a boo until you feel like it’s safe to come out.
if you ask me a question then I’m going to ask you the same question . I must be as comfortable with you as you are with me. it won’t work if we are not on the same level.

[woodliceworm]

There is much value in this advice, the takeaway here is to be relaxed relaxed relaxed and to be friendly. In my meetings with people, not just on a few dates I have found two things help, you will have to listen, (that is in depth listening) and if you listen two things happen 1- you are most likely the first person to listen to them in ages and 2 they will tell you everything, you won't need to ask questions. You need to be respectful regardless of how you are treated even if you are treated badly - it's only date after all.
April does provide well-thought-out options that are worth thinking about in advance, should one be favored by the gods to engage in a date sometime this century. If not the careful approach to interacting with others will work well in other situations.

[ginnybenett]

I asked the question of what funny movie ? I observed he seemed offput and said he didn't have a movie. I pushed and asked was there one movie that really made you laugh, again he wouldn't answer, said any funny movie. I thought that was very odd. He was talking about his date from online and mentioned that she ordered the most expensive thing on the menu. To me that was red flag. He was accomplished, good high level position, shouldn't be caring about cost of a meal. I was willing to go on second date but he texted me that he met someone else that he had "great chemistry" with . I let him know I was happy for him and thanked him for letting me know - then I thanked God for making the decision for me LOL.

[brazidas]

Over the years a have been on lots of dates and the pleasant ones are when we are relax and the woman is not making it like a job interview. I actually had one woman give a 20 point questioner. Needles to say I did not have a second date with that woman. LOL

[kathryncothern]

I just love April…everything from her presentation and communication style, her valuable tidbits, her approach, and overall common sense approach. Always love when you have her as a guest Silke. ❤

[michellehermann]

What if YOU had rough childhood? Make assumptions at one’s values based upon their childhood may be a huge mistake. If the person doesn’t dig deeper, that may lead to inaccurate info.

[farmerbobsgarden]

i had to watch this 3 times. every time April brought up another subject, i found myself thinking about how i would respond to that question, and then i had to go back and listen to her response.

[magsteel]

I don't agree that "relationship" equates to "willingness to take responsibility for someone else". A relationship is whatever I want it to be.

[charlottehanna]

58 yr.old woman, single, thanks you. I'm not sure what to do these days. I do not blame my former spouse for our marriage having been a failure from day one, we were just blind to the real reality of what a real relationship/marriage is. It didn't go as I had fantasized. I divorced the situation 13 yrs. in so that we could both be free to explore/mature and move on. It's been 22 yrs. I'm not to sure what to do anymore. I do hope that I can connect with a man that isn't the average Joe that urinates all over the toilet. I need more mind power from the one that I will commit to.