Home Uncategorized 90 Online Dating Questions to Ask First So You Don’t End Up Meeting a Psycho

90 Online Dating Questions to Ask First So You Don’t End Up Meeting a Psycho

by Roberto
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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.

Looking For Love

Photo credit: Depositphotos.

First of all, without a doubt, it’s hard to find places in real life actually to 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 embarrassed 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.

The 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.

So here’s a small list.




Ok Cupid



The Dating Group

The League

Ok, now for the fun stuff!!

90+ Best Online Dating Questions To Ask Him


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 painstaking, 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 superpower 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 do?

Toilet paper rollover 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?

Do you 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, and 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/work out?

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 independent 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?

So many questions, so little time


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, and 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!

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

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