Twenty Questions – how to avoid dating problems

Twenty Questions – how to avoid dating problems

Over the last few years, I’ve gotten thousands of letters from you wonderful people.  And while the topics have covered everything from pets to parenting and music to morals, the vast majority have been about romance.  Dating, Crushes, Marriage, even Divorce.

And so often, I find you guys in relationships you probably shouldn’t be in.  The sorts you could have avoided by asking the right questions (or at least have gotten out sooner if you had).  Which then keep you from the wonderful love stories you deserve.


So I’ve put together a list.  Twenty Questions to ask yourself before you date.  Some of these are probably easy, some are likely very hard, and definitely many of your answers will change as you grow older.

And while I can’t guarantee that doing this questionnaire will bring you the fairy tale romance of your dreams, it should help you avoid most of the problems I’ve seen in your letters.

So take a shot at it, and see what you think!


The first two are simple and shallow – before you consider dating anyone:


  1. WHAT ARE YOUR TYPES? No one is attracted to everyone – or even to everyone considered “attractive.”  Some people have extremely specific attractions (only tall blonde altos, or only muscle-bound nerds), but even when you’re very young, you’ll know there are certain qualities that attract you.  Height, skin color, hair or eye color, thin or curvy, hairy or not; I know a woman who refused to date any man whose feet were smaller than hers.  And you might even find looks aren’t as important to you as scent, or the sound of someone’s voice.  Whatever your criteria are, it’s great to be aware of what matters to you – and what doesn’t.


  1. HOW MUCH TOGETHERNESS DO YOU WANT/NEED? Oh I see this one all the time.  One partner texts ten times an hour, the other wants to check in once a day.  Both are fine, but maybe not good for each other.  Or one person wants to be touching all the time, while the other needs more space and just wants occasional physical contact.  Or one loves touching but not in public, which makes the other feel rejected.  And then of course issues arise where one partner wants “to go further” than the other, at least at that particular stage of the relationship.  Know what you want and need in these areas, and speak up about it.  You’d be amazed how many problems that’ll solve.



Then this next bunch matter when you actually become a couple – even if just for a short time.


  1. HOW DO YOU WANT TO BE TREATED? I know, that sounds vague.  But look at the couples around you.  Some are so kind and gentle with each other, and never say anything sarcastic.  Some tease a lot.  Some are always talking about each other or referring to each other, while others feel better not doing that, and just knowing the other is there for them.  Some like to fight and then make up, while others only complain in very careful soft language.  All are fine.  But who are you?  I see so many – just as an example – young women who say they want to be treated with chivalrous kindness, and then choose Bad Boys every time.  So be honest about yourself – for example, I don’t like dogs attacking me, but a little playful biting is fun!


  1. WHAT’S THE WORST FEELING FOR YOU? I’m not asking about your greatest fear necessarily, but rather something you actually experience.  For example, I hate being left alone, I hate baths, and I hate feeling I’ve hurt someone I love.  Now all those do happen at times, but I’m sure glad I don’t live with a person who’ll leave me alone for a week at a time, or give me a bath every day, or scream at me that I’ve ruined his life!  So if what feels worst to you is being ignored, you probably shouldn’t date the super-ambitious student working 20 hour days to get perfect grades, while on a top sports team, and working three jobs to pay bills.  They’re a great person, but likely not what you need.


  1. WHAT’S THE BEST FEELING FOR YOU? How often do I see someone who loves, oh, for example, singing on stage.  And they pair up with someone who finds that dumb or cheap, and wants them to stop doing it.  WHY WOULD ANYONE DO THAT?!  Don’t choose someone who won’t tolerate what you love most, or you’ll have to make an awful decision, choosing between them.


  1. HOW DO YOU DEFINE FAITHFULNESS? Do you feel cheated on if your boyfriend or girlfriend is talking to someone else?  What about if they hug them?  Kiss them?  Date them?  There’s no right answer to this – what matters is what you feel.  Be sure to date someone with a definition similar to yours.  Otherwise it’s just guaranteed to be a mess.


  1. WHAT DO YOU NEED RESPECTED? Imagine if a great athlete met someone she was fully attracted to, they had great times together, all was fine… but that person felt that a career of playing sports was really pathetic and childish.  Imagine if you cared a lot about great art, and your partner considered that stupid.  There’s nothing wrong with having different interests – it’s really fun – but there are things you need respected in your life.  Maybe your family, or your job, or your hobby.  Don’t fill your life up with someone who doesn’t respect what you care most about.


  1. HOW LONG DO YOU WANT YOUR NEXT RELATIONSHIP TO LAST? Are you looking for a fun weekend?  A summer fling?  A full commitment?  You are begging for heartbreak and frustration if you haven’t thought about this, and aren’t expressing it to someone you date.  Make sure you’re on the same page.


Now if you’re after a short-term thing, maybe that’s all the questions you’ll need.  But if you’re looking at a longer haul…


  1. WHAT DO YOU VALUE MOST? This might be different from the “respect” question I asked before.  Maybe you care a lot about the environment, or about culture, or life, or honesty, or God.  A long-term relationship is doomed  if the two people don’t share the same basic values.  This is different from having the same Opinions though.  For example, if you think all dog-kickers should be executed, you could have a happy relationship with someone who thinks they should only be jailed.  But you’re going to have a rotten time with someone who thinks they should be given medals.


  1. WHAT PLACE DOES RELIGION HAVE IN YOUR LIFE? This should be an obvious one.  Especially if you’re considering raising children.  If you are deeply devout, you should be with someone who is as well.  And if you’re a casual thinker about deep topics, it’s best you pair up with someone who feels that way too.  And definitely, if you’re an adamant Atheist, insisting there can’t be anything more than what we see, you’ll have a horrible time with a true believer.  You might find you’re able to enjoy someone whose religion is different from yours (though that’s not very recommended), but at least have the same attitude about it, and you’ve got a chance.


  1. WHAT PLACE DOES POLITICS OR PHILOSOPHY HAVE IN YOUR LIFE? Similarly, if you are planning on devoting a year to volunteering for a political campaign, life will be easier if you’re with someone who feels the same.  But if you don’t care much about social issues, then life will be easiest if you aren’t awakened every day with questions about how you feel about some argument you’ve never heard of!


  1. WHAT DO YOU HAVE NO RESPECT FOR? Remember my earlier question about how important it is that your partner respects what matters to you?  Well, what about the other way around?  Don’t bother dating someone who spends four hours a night playing video games if you think those games are idiotic.  Don’t date someone who writes romance novels if you find them boring, or beneath you.  Find someone you respect, whose interests you respect, and happiness is a lot more possible.


  1. WHAT TASTES MATTER? We all have tastes that matter to us.  So you’ve found someone who loves music, just as you do, but they find the rap you’re an expert on “just noise!”  Or they hear nothing in the classical music you treasure but “bedtime.”  Do you really want to live the rest of your life not blasting your favorite tunes out?  Or sharing your favorite books with your spouse?  Or crying at that favorite movie every year?


  1. WHAT LIFESTYLE MATTERS? Are you a vegetarian?  Do you like to keep the temperature in your home a little colder or warmer?  Do you like to spend a lot of time outdoors?  Do you love watching sports?  Do you like to play music loud?  Do your ears get hurt easily?  Again, the more you can determine of what matters to you, the better?


  1. HOW CLEAN AND ORGANIZED DO YOU NEED YOUR WORLD TO BE? It is hard  to live with someone who is either way more clean and organized or way less than you.  Sure you can disagree on some details (“I’ll keep the books in alphabetical order, if you do the daily dusting”) but overall it’s really a big deal that you’re happy and comfortable in the same sort of home.


  1. WHAT DO YOU WANT TO DO WITH YOUR LIFE? Do you want to retreat to a cabin in the woods and avoid civilization?  Do you want to work hard and get rich and live in high society?  Do you want to write a book or a symphony?  Do you want to become famous?  TALK about these things with that person.  Even if you never succeed at your goal, your trying it will either make your lives together heaven or hell.


  1. DO YOU WANT MARRIAGE? WHEN?  This one ought to be pretty self-explanatory.  If one of you wants it and the other doesn’t, we have a problem.


  1. DO YOU WANT CHILDREN? WHEN?  Same exact thing:  This one ought to be pretty self-explanatory.  If one of you wants it and the other doesn’t, we have a problem.


  1. DO YOU WANT PETS? WHEN?  This one ought to be as obvious as those last two, but I find couples getting together without ever discussing whether their family should include a wonderful dog or a stinky cat or some pretty goldfish, or…  Come on, talk about it!


  1. WHEN DO THESE THINGS NOT MATTER? And in the end, it’s impossible to meet someone who’s ‘perfect’ for you in every way.  You’re going to have to compromise on some things.  What are the items here that aren’t really dealbreakers for you?  How would a person need to be in order for you to give up on those?  Really, they have  to want to watch that rom-com with you every Christmas?  You can’t  tolerate their goldfish?

This last one is hard, and you won’t know it till you’re in it.  But it is maybe the most important question here.  Because, when you know exactly what it is that you want and need, but have found someone so wonderful that you’re willing to give up on some of those… there’s a really good chance you’ve found The Right One.


When Handsome was looking in the pound for a new dog, he wanted someone younger than me, smaller than me, and with shorter hair.  But I won him over, and that was that.

So find someone that great, and start compromising.  There’s nothing better.  As that beautiful old song sings, “Then go to her side, and make her your own, or all through your life you will live all alone.  Once you have found her, never let her go.”

(Or him, or them, or it, or…!)



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Leave a Reply 2 comments

Baraka - March 11, 2019 Reply

I so wish our DV clients learned these 20 questions before they got out of elementary school.

    shirelle - March 13, 2019 Reply

    Oh Baraka what a wonderful compliment! Thanks! I wish it hadn’t taken me so long to figure them out as well!!!

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