I have, in the past, been a serial dater. For the longest time I thought if I just dated 2 or 3 women per week I would find the woman I could spend the rest of my life with.
This mindset did lead to me dating hundreds of wonderful and beautiful women over several years but as an approach, it was woefully ignorant.
I guess I adopted the mindset because my dad married his first girlfriend (my mom) and then when they were divorced he married his next girlfriend. I grew up in a stable home but without the shining example of a great relationship.
That all changed a few years ago when I met someone I thought was “the one”. Her and I clicked on so many levels. We could talk for hours about everything and nothing. The sex was fire. We had a deeply respectful friendship and bond.
However, we made some pretty important mistakes. Looking back now, I realize we were more surface level than anything. “The one” and I had it all figured out but didn’t dive deep enough into the stuff that matters, and by the time we started, it was too late.
Now, single again, I realize it is the grey area—the ambiguity, the maybe’s, the shoulder shrugs, the hold back’s—that matter most if you want to build a life with someone.
With that in mind, I spent many a nights curating this list of dire questions you must ask someone you are in a relationship with before popping the question.
WARNING: This post takes the romanticism out of relationships but if you discuss these things at the right times they can be pleasant conversations that bring you together.
What are your plans for money, debt and savings?
A lot of relationships fall apart because of finances.
I find that’s often because they are tied to habits and trust. You should be able to talk about what you make, what you think you’ll make, how much debt you have, and what your savings plan is.
If you take these conversations seriously and offer complete openness your relationship is less likely to collapse for the same reasons as many others. Plan together, budget together … spend together.
What demons are hiding in your closet?
This is a particularly hard question to handle because it is so deeply personal.
You can’t expect someone to air all of their demons immediately as it is likely whatever they are going to tell you, they have never told another living soul.
Don’t hold back!
You can only be truly happy with someone if you’re not holding back.
What does your work life look like? Will it get easier or harder if things go to plan?
We’re all at different stages in our life plans. Personally, I’m at a stage where I have a bit more freedom from my office. If things go to plan then it is likely that my life will get easier.
However, I might meet a woman who is just starting out in law school. Her life is going to get harder.
What does that look like and how will you handle the differences?
Are you willing to fully commit?
There is no room for wishy-washy bullshit when you’re in a relationship. If the level of commitment doesn’t match, end things.
Don’t wait around for them to change their mind. Be honest and upfront from go about what you’re looking for. If it’s just sex, say that. If it’s love, say that. If it’s a partnership without marriage, say that.
What does social media look like?
People break up because of social media habits all the time.
Talk about how much you want to share about your relationship and what acceptable communication looks like. Some people see liking cover model’s posts as passive cheating, some don’t care. Define it.
What is the acceptable level of risk?
I am a risk taker; jumping out of planes, taking crazy chances in business and with my money, and I’m just not scared of uncertainty.
But, I’m also aware that most people don’t have the stomach for that kind of lifestyle. You must define what level of risk is acceptable so that you’re not constantly alienating each other.
Does your energy match?
This one can be confusing because similar and opposite energy can be compatible. Often times though, opposite energy starts to grind on the more introverted person’s gears.
Stick to your instincts on this.
I know a couple who based their relationship around their energy (he’s manly and tough, she’s cute and spunky). They are incredibly happy. My friend told me he never knew how important energy could be until he met her.
Think about the type of mate you want. For me, it’s a more traditional and sweet woman. I’ve dated a lot of modern hard-asses. I knew those relationships wouldn’t work and now, in hindsight, I know why.
Big wedding or small wedding?
I’ve read studies that put the number of couples breaking up while planning their wedding as high as 30%.
“The one” and I spent hours on a road trip planning our wedding for fun. It was nice to know we were on the same page, and that what we didn’t agree on wasn’t all that important. Talk this out or risk mailing invitations for a non-event.
What is your stance on kids?
Do you want to have kids?
Can you have kids?
If not, do you want to adopt?
Are kids completely off the table?
I once went out with a female who asked me about kids on our first date. I was put off by this at the time but I now realize that having kids were her number 1 priority, and as such she was making sure we were aligned.
We weren’t, and I now appreciate her approach.
I also think it’s good to talk about parenting styles if you agree that you want kids.
What is your medical history?
This is a very uncomfortable subject for me. I don’t like talking about some of the gross stuff that our bodies can do, but it is important that you both know your medical histories.
This needs to include family history and even the dreaded STD talk. Make a plan around this so that there is no guesswork.
If you get married, you will be relied upon to make decisions if the other can’t. Also, go to medical appointments together when you can.
What are your plans for 1, 5, 10, 50 years into the future?
Make sure they somewhat align, especially retirement plans. I know of a marriage that failed because they realized too late that one wanted to retire to the country and live a simple life close to home, and the other wanted to travel and die as far away from home as possible. If you’re building a future together you need to be on the same page. If not, that’s a great indication that you should part as friends.
What role does religion play?
This is a biggie!
I’m agnostic but I have dated Catholics, Christians and Muslims. I could never date an atheist because I find their certainty to be ignorant.
Religion has become an issue twice for my past relationships and it was never the simple act of belief, but rather the constant attempts to get me on their side of the cross.
Religion is often tied to a person’s moral, ethical and decision making character so violating this will have dire consequences.
What are the core beliefs regarding forces that guide our lives?
One’s belief in destiny can mold their entire being. While one’s belief that we make our own fate can mold their entire being.
I find those that believe in destiny are usually more spiritual.
Talk about this.
If your partner believes in fate, it means they are less likely to take action and will often leave it up to the universe.
If your partner doesn’t, they might be annoyingly persistent; TOO annoyingly persistent. *insert hands up emoji*
Do you have anger issues, anxiety or depression?
It’s okay if you do, but you should be upfront about it.
Go deep.
Your partner should help you understand what your life is like with your condition, and you in turn, should work to understand if you can survive under those circumstances.
And, if you do have these issues, you should be willing to get help or you’re not mature enough to be in a relationship. In sickness and in health, but that doesn’t mean you should put unnecessary burden on another.
Are you sexually compatible?
I absolutely detest when someone calls me vein for only dating beautiful, slim women. What would you prefer? That I date women I’m not attracted to?
My cousin likes thick women. Would you give him shit for calling the women I date sticks?
Sexual compatibility is critical because it extends outside of the bedroom. If you’re sexually compatible you’re likely to be more affectionate and affection is often all we need to change our moods.
A piece of the sexual puzzle should be consent. I know that some of you might call me a snow flake, but it’s true. Set really rigid rules in this regard so that you don’t end up in a situation you can never come back from.
Think Walter White in Breaking Bad. People discount the importance of the scene where he basically rapes his wife.
Do You Have Similar Interests?
This may seem like a no-brainer, but so many people start dating because of attraction and then barely hold on to a thread of common interest.
You can have separate interests but you should have more in common than you do, not.
Also, talk about experimentation; in the bedroom, in life experience. Experimentation is how couples keep things interesting after you learn everything there is to know. Think about when you first meet; it’s all so new and exciting. Keep it exciting!
How important is family acceptance?
I’ve dated and was engaged to a woman that cared deeply about how their family reacted to the man in their life.
I’ve also dated women who couldn’t care less.
Figure this out and if family acceptance matters, and you’re not the one that your better half can bring home then work on it.
I’ve seen many relationships die because if you cause in-fighting, you will likely lose eventually. Even if you win, and your partner chooses you over their family, you still lose because your partner will be affected negatively by the choice.
What is your disagreement plan?
Think of a long-term relationship where you didn’t disagree. I’ll wait.
It’s funny how we all know we will do battle with our significant other but we don’t really plan for how to deal with it. Most couples just get heated, yell, say things they don’t mean; wash, rinse, repeat.
You need a plan for these moments.
I dated a woman who came up with an amazing plan and I strongly suggest it. When things were about to get heated, we’d say, “truce” and then separate to write down what we thought. We then exchanged the letters and wrote what we thought after seeing their side.
It worked incredibly well and stopped many fights.
What are the plans for parents in old age?
Here’s a sensitive topic for some reason.
Many couples argue about what to do with their parents when they get older and can’t provide for themselves. Make a plan and make sure you’re both on board with it. This is important. No one should have to live with the guilt of not being there for the people that raised them because of their partner.
It will eat your relationship alive.
What are your differences? What do they mean now and later?
I, for one, believe age doesn’t matter much. I’ve dated mature 25 year old women and immature 45 year old women. No, age doesn’t matter but effects of age do! This is just one difference that we all confront often.
Be honest about your differences and how they do and will affect your relationship. It’s okay to back away because of them but it’s better to back away before marriage.
What is acceptable behaviour among the opposite sex?
Please remember, I’m writing this from the view of a straight male. I don’t even know if these questions apply to gay or lesbian couples. I’m not excluding you, I just don’t know enough.
That said, it’s important to establish what is acceptable behaviour with the opposite sex in the eyes of your partner. The spectrum is wildly varied.
Personally, I think you shouldn’t do anything with a member of the opposite sex you wouldn’t feel comfortable doing if your partner were standing right there.
Some are are way more liberal and can handle their partner going in for long hugs with ass smacks. Some, won’t even like hugging.
This is why it’s an important question to ask. What’s ok? What’s not?
What happens if the best laid plans are blown apart?
It happens all the time—life throws you a curveball. Maybe you lose your job. Perhaps you lose a parent. You could even be injured.
What happens when things fall apart?
You must talk about how you are willing to support each other so WHEN the time comes that you need to lean on each other, you don’t end up falling over and breaking something.
What is your role?
Here’s a big one filled with a lot of small issues.
What is your role in the relationship?
What is your partner’s?
What are the daily, weekly, monthly, and lifelong expectations for each other?
Identifying roles is the best way to avoid confusion and frustration. This applies to chores, taxes, maintenance, gifts, plans, etc. Identify who does what and what you’ll do together.
There is nothing worse than 2 people fighting over who will do the taxes and then getting audited due to late submissions. Just remember, when you pick the roles, ensure they play to the individual’s strengths.
Are you open to dealing with insecurities?
As much as we’d like to believe that we can leave the past in the past, it’s just not possible.
We all come with our own set of baggage. Some people have a carry-on and some exceed the maximum weight limit. That baggage will bring about insecurities.
A common mistake is to get mad when someone is vulnerable in a relationship.
Are you willing to give up your password to your phone?
Are you willing to snap a pic when they ask where you are?
If you’re open about these things, the requests will fade away over time as the trust builds.
But are you willing?
What is cheating?
This might be the number one reason I have seen relationships fail.
Not properly defining what cheating is to each of you is a costly mistake. Is it sex? Is it flirting? Is it a massage? Is it hugging? We all have different ideas about what we find acceptable.
Make sure you know.
What is physical and verbal abuse?
I had a friend who once choked his girlfriend in bed. His past girlfriends loved it so he assumed she would too. It ended up being the kiss of death for them because—as it turned out—he couldn’t have sex without some form of BDSM involved. He didn’t even realize until he slept with her.
She saw this as physical abuse.
If they had talked it out, they would have been able to end things early, instead of with one personal crying in bed and the other frustrated to no end.
Some couples can openly make fun of each other, and some just can’t.
You need to find out where the line is between fun/kink and abuse. Establish it early and never cross it.
What are you wishes in the event of a major issue?
If you’re going to marry someone, each of you should know the other’s final wishes.
Not just final, but what if you end up in a coma or incapacitated in some other way? What does your partner want in terms of a DNR?
This is all uncomfortable conversation but it is required to ensure you are respectful of your partner’s needs.
What is love and how do you feel it?
Love is different for everyone.
For some, love is grand romantic gestures. For others, it’s reading on the couch while playing footsie. There are literally billions of types of love and they are compacted into the five love languages.
The book on this topic is incredible and I think every couple should read it. Figure out how your significant other wants to be loved and love them like that as long as they’ll do the same for you.
What is fun to you?
For me, fun is extreme sports, skydiving, trying new things, and exploring culinary delights. I also like to occasionally Netflix and chill. From time to time, fun for me is planning big romantic gestures.
However, I don’t like trying out of the box foods or playing frisbee.
That’s what fun is to me.
What’s fun to you?
Okay, now tell your partner. It is absolutely essential that we can have fun together in our relationships. Not only will you be happier together but fun has health benefits (unless your parachute doesn’t open).
What is your healing process?
We all have different ways of healing from trauma.
Some shut down, some need to talk, some need a drink … there are endless possibilities. Talk about each other’s healing processes and NEVER stand in the way of it.
If you can’t handle how they heal, you can’t handle them.
When the hard times hit, what are you willing to do to repair damage?
We all have our breaking points. Each of us can handle only so much before we say, “ENOUGH!”
What are yours and what are your partner’s?
As an entrepreneur, I am constantly dealing with up’s and down’s. When the down’s hit, I’d rather downsize than ask my partner to burden herself.
However, some think the burden is part of a healthy relationship. Figure out where the line is and draw it into the cement.
Are you a conspiracy theorist?
I saved this one for last because it’s a new entry into my lexicon but I believe it to be important, especially when major world issues like COVID-19 hit.
Does your partner believe everything is a conspiracy, while you believe in evidence and science? That will be a problem later on.
Think about living with someone right now who refuses to take COVID-19 precautions and thinks Bill Gates made the whole thing up.
That could easily break a relationship.
So, obviously “the one” wasn’t actually thee one. She was training. She was a way to figure out how to be a better man for my next relationship, which I really hope is my last. Dating sucks in 2020.
Did I leave anything out? Do you agree with these questions? I’m curious. Let me know.
