Meeting Someone New: Questions to Ask Before It’s Too Late

For those of us like myself who are in the dance of enjoying the single life and occasionally meeting people with that sense of mutual attraction: there are questions that need to be asked!

Again, in the “for those of us like myself” I do mean middle-aged (it hurts to qualify myself as such), with some form of  multiple relationship history.

First off: you meet a single middle-aged person who’s never been in a real relationship lasting longer than a year – just turn around and walk away. It’s not a good sign. Not that a past with failed relationship is so much more sparkly but at least it shows that someone has taken a chance on love and given their heart to someone else even if it meant running the risk of having it pulled apart.

What questions should you ask a potential new mate? Read on my friend!

Start with the obvious: what are you passionate about?

There needs to be passion. Has to be! A person without passion, and I honestly don’t care what that source is, it can be watching old black and white movies in the dead of night, hanging out in public libraries and browsing through old encyclopedias, or rummaging through yard sales… A person needs a passion otherwise they’ll be looking to you for everything. A passion in life is as essential as spices in cooking.

What was-were the catalyst-s to ending your previous relationship(s)?

We always repeat our own history. We pick the same kind of wrong person and we assume we’ve learned and grown, but we fall back into old patterns. If everybody answers this one as honestly as possible, even if it means scaring the potential new mate away, then better be safe than sorry. If you can tolerate their flaws now, you’ll have a better grasp and understanding of them once stuff starts getting serious.

What’s your favorite and least favorite kind of music?

What if… your potentially soon to be better half thinks muzak is the best thing in the world? And you would end up stuck having to listen to elevator music every single day for the rest of your life? No. End that madness before it even starts! Or worst, what if Angus and Julia Stone are the equivalent to fingernails on a chalkboard to him or her? Turn around, and walk away.

If you could go back in time, and do something different, what would it be?

I think we learn a lot from people’s past regrets. Some have none: kudos to them! But for the norm, most do have at least one regret. This will be a delicious insight into someone’s darker side. If you can love someone’s dark side, oh the happy sides will be such chocolate pudding filled with Kahlua!

If your 15-yr old self could see you today: what would he or she have to say to you?

I firmly believe we shape all our dreams and aspirations at the age of 15. It’s that middle zone between being a kid and someone who’s almost old enough to be considered an adult. It’s also at that age where we have such perfect opinions on how to make the world a better place. Fifteen year olds see and understand so much more than most give credit for. Every 15-yr old is an artist in the making.

Would their 15-yr old self scream at them for having wasted their lives? Or would they high five them for being so überly cool throughout? Yeah, I always want to know that one and firmly believe my 15-yr old self would be thrilled like a kid at Disneyland to see the life I’ve lived!

What are your daily habits/rituals?

Some people need plenty of me time. Before going to work they may like to meditate, do yoga, workout, write (I’m talking about myself here).

Some only drink on weekends with friends, others like a glass of wine after work every day. Drinking can be a major issue! Some fall asleep in front of the tv. Others may absolutely hate the unwanted TV noise. What a person does daily, man – that shit’s important! You can’t plan your life with someone who would annoy the crap out of you day in day out!

What’s your ideal vacation?

Oh boy. Another biggie. For some it’s spending the week on a golf course (barf) and others need the wildest adventure tour ever! Some want the group thing of hopping from one European country to the next each day and come back home two weeks later dead tired and not knowing a flick of any of the countries they visited because they simply rushed from one sightseeing spot to another.

I know couples that always spend their vacations apart because they don’t like the same things. How dreadful. I’m not saying a couple needs to spend every single day together, and I’m all for separate trips but come on, at least one nice good vacation together per year right?

What are your spending habits?

I think I read somewhere that one of the major reason people break up is because of money. One spends too much, the other is too frugal. One pays for everything, one never contributes.

You may want to clear that up before falling in love and moving in together, and realizing your new spouse owes over $20K in gambling debts and wants to take a cruise ship vacation because they have 24-hr casinos. Frightening.

Are you a clean freak or a slob?

Yikes! I know I could NOT live with a super clean freak. Someone who would yell at me for a crumb on the floor, or a fingerprint on the over-polished chrome fridge door. Then again, I would gag at the thought of a kitchen counter where I couldn’t even put my fork down without having to rinse it out with rubbing alcohol.

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I could go on. And on. But I’m afraid any potential future date of mine who may stumble upon my blog and see this would show up ready and primed as if coming for a job interview on our first meet up! I’m sure I missed some biggies, what do you think? What question would you want to ask if you could?