Senior Lifestyle

80 Senior Dating Questions: First Date Conversation Starters 

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Are you a senior looking for some interesting senior dating questions to keep a date fun?

As a dating expert, I know some speed dating questions to avoid awkward silences on a date.

Read this list of 80+ first-date questions, along with tips, to ensure you don’t bore your date.

Senior First Date: How to Break the Ice

You are never too old to learn from someone young. Intergenerational relationships are vital for keeping growth within society, and being a life-long learner has several benefits.

How do you successfully break the ice on a date? Relationship coach Varsha Martha suggests starting lightly (1).

She says, “Asking questions that require black and white answers is a great way to start deeper conversations.”

You could have finally had your chance at older singles meetups and met a compatible person.

senior dating on a coffee shop

Speed dating for seniors is an exciting and novel way to meet new people. However, with limited time on each “date,” making a memorable first impression is crucial.

But to boost the likelihood that they like you, what you talk about needs to be fun, interactive, and intriguing. Here are some methods to break the ice when engaging in speed dating for seniors:

1. Tell a Funny Joke

Funny jokes could make your date crack up, making it easier to start a conversation. Humour has never let me down in diffusing a potentially awkward situation. 

2. Compliment your Date

Compliments from the heart can make someone mellow and calm down for deep conversations later. It could be about a piece of clothing they’re wearing or even their perfume.

3. Ask a Fun Question

Fun questions are excellent conversation starters. They are my favorite tool when I can’t quickly come up with a funny joke to break the ice. 

4. Ask About their Online Dating Profile

The world of technology has made it easier to find people online. Sites such as eHarmony and Silver Singles make it easy to find dates.

So, when you meet such a person on a date, asking about something on their profile could be the perfect icebreaker.

Most people have some fun stuff on their online dating profiles. That could help you with an icebreaker for meeting them in person.

5. Share an Experience

Do you have a fun or strange experience you can share to pique curiosity in someone? Why not use that to break the ice with your date? 

Doing it well could help you avoid awkward moments at the start of your date.

6. Ask About Pets

Pets are the favorite subject for most pet lovers. So breaking the ice by asking your date about pets is an excellent way to get a head start. 


Ask them if they are a dog or cat person. If they are any of them, then you’ll have hit a perfect conversation spot and avoid the quiet times.

7. Ask about the Latest Concert They’ve Been To

Music is a fun topic to bond over, especially if you have the same music taste. That’s why this question is a perfect icebreaker.

The last or best concert your date went to will tell you something about their music taste. And from that could come an arsenal of ideas about other questions.

8. Ask Who’s Their Role Model

Most people have someone they admire. Maybe they have unique relationships with them or love their accomplishments in life. 

That gives you a clear idea of the essential people in their lives. It also gives you an insight into their personality.

9. Ask About their Dream Job

Most people have an absolute dream job they’d wish to have at least once. So asking about that could be an ah-ha moment that gets you to start a conversation fast.

10. Ask About Their Bucket List

It’s normal for people to have a list of things crazy or not they want to do before the end of their life. You can barely put a foot wrong asking your date about their bucket list.

80 Senior Dating Questions: Including Speed Dating

There are many types of questions you can ask on a date. To make it easy for you, ill categorize them into different settings.

matured man and woman dating and drinking together

10 Romantic Questions to Ask on a First Date

  1. What is your take on love at first sight? Do you think it exists?
  2. Do you prefer texts or calls?
  3. What’s your ideal dating type?
  4. How fast do you fall in love?
  5. What instantly gets you attracted to someone?
  6. Are you a romantic?
  7. What’s your nickname? Am I allowed to give you one?
  8. What’s your take on matters of love?
  9. What’s the most romantic thing someone has ever done for you?
  10. Would you kiss someone on the first date?

10 General First Date Questions

  1. Are you a night owl or a morning person?
  2. What’s your pet peeve?
  3. What’s your favorite piece of advice?
  4. Which is your favorite dating app?
  5. What is your favorite food?
  6. How’s your social life?
  7. What do you do in your spare time?
  8. What is your ideal vacation?
  9. What’s your biggest fear?
  10. Do you believe in zodiac signs?

10 Funny First Date Questions

Besides starting a funny joke, asking someone a funny question could set the ball rolling. 

  1. What do you think is the ugliest animal alive?
  2. What’s the most stupid thing you’ve ever done for love?
  3. Do you ever want to set yourself on fire?
  4. What makes you laugh?
  5. Do you trust your gut or prefer a second opinion?
  6. What’s the worst date you’ve ever been to?
  7. What’s the funniest song you’ve ever listened to?
  8. What type of person are you?
  9. Do you have a favorite piece of furniture?
  10. What was your most embarrassing moment?

10 Everyday Life Questions

These questions wouldn’t qualify as the deep questions you can ask a date. But they are perfect for getting the conversation going.

  1. What’s your favorite band?
  2. What’s your favorite season?
  3. What household chores do you hate the most?
  4. What’s your typical workday?
  5. What’s your worst nightmare?
  6. Are you an anxious person?
  7. What is your wildest dream?
  8. What keeps you going?
  9. What’s your favorite karaoke song?
  10. Are you an animal person?

10 Best Speed Dating Prompts

According to dating expert Julie Spira, speed dating has seen an increase in the recent past (2). That increases the need for speed dating questions.

 This list of questions will give you an arsenal of ideas to use.

  1. What’s the first thing you noticed about me when you saw me?
  2. Who is your favorite musician, and why?
  3. What’s the weirdest food you’ve ever eaten?
  4. What is the strangest place you’ve ever been to?
  5. What’s the worst concert you ever went to?
  6. What are your favorite movies?
  7. What country’s food is your favorite?
  8. What’s the most amazing adventure you’ve ever been on?
  9. Do you have a sweet tooth?
  10. Have you done or considered skydiving?

10 Personal Questions to Ask on a Seniors First Date

Sometimes you need personal talking points for the first date. These talking points help you connect with your dater faster and know what drives them.

  1. What’s your absolute relationship deal-breaker?
  2. Do you prefer a short or long-term relationship?
  3. What’s your biggest accomplishment in life?
  4. What’s your marriage history?
  5. What makes you happy?
  6. Who are you most thankful to in your life?
  7. Are you a religious person?
  8. Which fictional character do you most see yourself as?
  9. What’s your favorite family vacation?
  10. What’s your best character trait?

10 First Date Questions to Ask a Senior Male

  1. How old do you think I am?
  2. Do you have a celebrity crush? Who?
  3. At what age did you have the most fun?
  4. What is your favorite international food?
  5. What’s your ideal date: outdoors or an indoor movie night?
  6. What’s your favorite childhood memory?
  7. Do you have an irrational fear?
  8. Iron man or Spider man?
  9. Where do you see yourself in ten years?
  10. Do you love video games?

10 First Date Questions to Ask A Senior Female

  1. What’s your perfect Sunday?
  2. What are you most passionate about?
  3. For how long have you been single?
  4. Are you a country or city girl?
  5. Do you love children?
  6. Are you the adventurous type?
  7. Which animal do you think represents you the most?
  8. What’s your ideal romantic getaway?
  9. What do you love most about speed dating?
  10. Which place would you love to travel to the most?


What should you not do on a first date?

Never talk over your date, don’t dominate the conversations, and don’t constantly talk about yourself. Also, don’t always be on the phone.
There are a ton of things you shouldn’t do on your first date. Remember, the rules of common courtesy still apply on a date.

Are deep, personal questions good to ask on a date?

Yes! But it is important to read the body language of your date is important to know where the boundaries are. 


Remove the worry from senior dating questions by using some of our ideas on making a date lively from this list without memorizing it, as that is a bad idea.

senior couple laughing

Do you know any other interesting questions that would be perfect for a senior’s first date? Share them below, and we will add them to the list.


  • 1. Login • Instagram [Internet]. www.instagram.com. [cited 2022 Aug 10]. Available from: https://www.instagram.com/coachingbyvarsha/?hl=en
  • 2. Spira J. Is Speed Dating Making a Comeback? [Internet]. Cyber-Dating Expert. 2022 [cited 2022 Aug 10]. Available from: https://cyberdatingexpert.com/speed-dating-comeback/

About Author

Lamia A Kader, MD
Lamia A Kader is a Medical Doctor and a Medical Research Professional with a Ph.D. in Clinical Research. ISMMS, USA. She had enhanced her medical knowledge of medical devices and equipment development and innovation by attending clinical meetings, local national courses, journal clubs, and conferences, in addition to e-learning, subscribing to major medical journals and keeping an eye on latest trends in medicine and keeping an eye on clinical trials industry and healthcare marketing current trends. She had participated in several medical device innovation projects by conducting clinical research studies, developing clinical trial protocols, writing patient safety narratives and “Medical Device Risk Assessment Reports” to transform new medical technologies into real products that save and improve lives. Follow her on LINKEDIN. Read her LATEST POSTS. Learn more about her HERE.

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