90+ Online Dating Questions To Ask Him: Funny And Serious!

Many of us women over 50 are just starting to dip our toes in the dating pool again and it can be kinda scary on so many levels. I figured a good place to start is by writing up this great resource for you of 90+ online dating questions to ask him, funny and serious.

Look, dating at any age can be stressful but when we’re in our 50’s and 60’s, oy. It’s beyond stressful.

You might really like these related articles:

What Women Want in a Man: 10 Things We Look For

Finding Love Over 50: 7 Things to Make it Easier

First of all, without a doubt, it’s hard to find places in real life to actually find someone to date so we head to our computers and check out a dating site or two. And there’s nothing wrong with that, at all.

So don’t feel embarassed or awkward or anything like that. I bet if you were to ask your best friend or even family members about online dating, many of them would say it’s totally cool and may even help you!

But there’s always a word of caution. Not all is what it seems on the internet. Always use caution and if you’re not sure about something or someone, ask a trusted friend/family member to help you.

Scammers are everywhere. That’s the sad reality. But there are also some really good men on dating sites too! Your potential partner might be there. Trust your intuition. If something feels off, it is off.

Even though I’ve given you over 90 of the best online dating questions to ask him, you have to know that some men will say what they think you want to hear and not answer them honestly.

So there’s that.

First thing I want to touch upon lightly is your online dating profile. While this blog isn’t about creating a profile, I do want to help you a teeny bit with this.

Creating Your Online Dating Profile

If this is your first time creating an online dating profile, it can be a little stressful, frustrating and unnerving. Just relax and have fun with it. I know it’s hard to talk about yourself.

Most online dating sites already have a bunch of really good questions for you to answer to describe yourself. Just be honest and clear.

And don’t be afraid to be upfront. If you hate men who smoke or drink, be very clear about it. You are NOT settling for second best girl. You want the best!

You also want to find someone with similar interests. No sense in wasting your time with a couch potato if you are an adventurous person, right?

If you need help with your profile, ring up your best friend to help you. Sometimes others see different qualities in us that we don’t!

But most importantly, just have fun with it.

Best Online Dating Apps

I thought I’d throw in a few of the best online dating apps to give you a little jump start.

Here’s a really good article from mindbodygreen.com that goes in great detail for all the apps.

So here’s a small list but def check out the article above!

E-Harmony
Tinder
Match
Ok Cupid
Hinge
Bumble
The Dating Group
The League

Ok now for the fun stuff!!

90+ Best Online Dating Questions To Ask Him

I’m gonna break this down into a few different categories to make it easy and organized.

Fun Questions
Deep Questions
Flirty Questions
Intimate Questions
Random Questions
More Random Questions

These will be in no particular order of importance. I think they’re all important questions. The getting to know you process is already long and pain staking, though it can be fun too, but I think when you ask the right questions it’s just a great way to get everything out in the open.

You also want to be as natural as possible and keep the conversation from sounding like a job interview! Haha!

First up, let’s do the fun questions!

15 Fun Online Dating Questions to Ask Him

What did you always want to be when you grew up?
What’s your favourite animal?
What’s your favourite band/song?
If you had a super power what would it be?
Do you sing while you’re driving/in the shower/cooking?
What food absolutely grosses you out?
What’s one weird thing you can do that no one else can?
Toilet paper roll over or under?
What’s the most bizarre place you’ve had sex?
What’s your favourite cartoon/childhood show?
Do you like splashing in puddles?
What’s the silliest thing you’ve ever done on a date?
If you could be a fictional character, who would it be?
Best place to travel is?
Car/boat/train or plane?

15 Deep Questions

Do you have a good relationship with your parents?
What’s the biggest fear you have?
Do you believe in God?
Do you stop and help homeless people when you see them on the street?
Do you have road rage? Anger problems?
Name one thing you can’t live without
How much time do you spend online?
Early bird or night owl?
Do you get along with your siblings/family?
What is your greatest weakness? Strength?
Doyou consider yourself a patient person?
Who is your role model?
How important is physical appearance?
What’s the worst thing that’s ever happened to you?
Do you hate anyone?

15 Flirty Questions

Do you like kissing?
Do you like getting/giving foot massages?
How do you feel about lingerie?
Are you a romantic guy?
Do you prefer morning/afternoon/evening sex?
What’s your favourite part of a woman’s body?
What is something that really turns you on be it music, a scent, whatever?
Do you get jealous quickly?
Shower/baths together or no?
How affectionate/touchy are you?
How long should foreplay last in your opinion?
How do you feel about adult toys?
Are you down for spontaneous sex?
Skinny dipping, yes or no?
Do you like to have/serve breakfast in bed and chill out?

15 Intimate Questions

What is your idea of a perfect date?
What is something a woman does you will truly love and appreciate?
How supportive can you be if your partner’s health fails?
Do you like cuddling and watching movies?
Do you like holding hands while going for walks?
Would you prefer to shop alone or with your partner?
Will you help with groceries, laundry, household chores?
Do you consider yourself a spiritual guy?
Do you like having cozy intimate dinners with friends and family?
What hurts you the most?
What makes you the happiest?
Do you believe in love at first sight?
Introvert/extrovert or ambivert?
Do you value family relations/loyalty/kindness?
Do you like star gazing?

15 Random Questions

This will include interesting questions, open-ended questions, maybe some more serious questions, etc.

Do you like to exercise/workout?
Do you like to eat healthy?
Do you like to travel?
Are you an eye for an eye kinda guy?
Do you hold a grudge?
Have your past relationships made you bitter or wiser?
What’s on your bucket list?
What’s your all time favorite movie?
What’s your favorite food?
What kind of music do you like listening to?
Do you have any pet peeves?
How do you feel about personal space?
Can you be relied on in case of emergency?
What’s your idea of a perfect first date?
How good are you at expressing your emotions/feelings?

A Few More Random Online Dating Questions To Ask Him

It’s no secret that online dating can be exhausting but remember it also can be a whole lot of fun too!! Don’t discount it until you’ve tried it.

What is your view of religion?
What are your political views?
Do you like kids?
How do you feel about volunteering your time?
How many women have you dated since your last serious relationship?
How long was your last relationship?
Do you want to get married again?
Are you a ‘what’s mine is mine and what’s yours is yours’ kinda guy?
How do you feel about independant women?
Do you consider yourself self confident?
How do you feel about small talk?
What is a good way to get to really know someone?
Do you have a good sense of humor?
Do you have any addictions/bad habits that are considered serious?
How open minded do you consider yourself to be?

And More Random Questions to Ask Him!!

Girl…there could be a million questions and that’s ok. You ask all the questions you need to. Heck you can even make up your own list of questions to ask to make sure you don’t miss anything that is important to you.

Personally, I think online dating allows for some of the best ways to get to know someone. It’s a safe place to ask all the questions you need to, engage in interesting conversation, get a feel of this person to see if they’re a good match.

And what’s not to like about going to one place and ‘shopping’ for Mr. Right? Seriously? Haha!

A few more questions you might want to ask could be related to:

his job/financial security
his family and upbringing
his children
his food and drink likes and dislikes
etc.

I mean. There’s just no end.

I do want to offer a word of warning though. Please if you see any red flags or have a suspicion that he may be lying or not telling the whole truth (deliberately keeping something from you) just walk away.

Don’t waste all your energy trying to figure someone out. If someone can’t be fully transparent and vulnerable, you will spend the rest of your time second guessing this person and lemme tell ya, that’s no way to be and will def not result in a happy relationship.

Happy dating!

ox iva xo

90+ Online Dating Questions To Ask Him: Funny and Serious!