I did a lot of online dating when it was brand new. In the process I discovered that the hardest part was weeding out the kind of person you don’t want in your life. Turns out it’s a lot harder than you think, particularly if one or both of your parents were toxic narcissists. Narcissism (and gaslighting & controlling behavior) is particularly hard to spot in the early stages of dating when people are putting their “best foot forward”, showing off the glossy magazine version of who they would like to be. So here are some conversation starters that help you spot what you don’t want & focus your attention on the kind of person you do want, by eliminating those “bad eggs”. The questions are also fun to talk about. Now, some people will think these questions are “too intense”. Naturally, those are just the sort of people you want to avoid. Why? Because Long Term Relationships (LTR) are intense and we need to go into them with eyes wide open. If you’re just looking for “fun” this is not an article for you…yet. But if even once, you’ve found yourself mired in a relationship that’s sucking the life out of you, or you’ve discovered how “un-fun” it can be to date a bunch of jerks, please read on.
1. Tell me about your sense of humor. What makes you laugh. What kind of jokes do you tell? What are some things you think are ‘unfunny’?
Reflections on meaning (RoM): Everyone’s sense of humor is slightly different, but a good LTR needs good laughs to diffuse tension and end senseless arguing. Plus, having someone in your life who can make you laugh just makes life better. So, knowing what makes your partner laugh & sharing what makes you laugh is not only fun conversation, it’s a key element in building a future. Weeding out: The last question is a window into people’s moral code. For example, I find racist, misogynistic, bigoted, and other hurtful humor completely unfunny. If a potential date was even tolerant of that sort of humor, I’d weed them out. Not interested. Not everyone will have analyzed or categorized their humor, but they should be able to give a few examples of what makes them laugh hardest. A person who will not or cannot answer question #1 is either a person who is hiding something, or someone who lacks self-reflection and insight. Even though the question is lighthearted, a non-answer would be good cause for weeding someone out.
2. If you could do anything to make the world a better place, what would it be? What do you do/have done to make the world a better place? Imagine an ideal world, what would it be like?
RoM: Question #2 is really about a person’s capacity to love. At the very least, imagining a world where all people feel safe, happy, and supported reflects a person’s ability to feel compassion for others. A person who is not interested in this question is, quite simply, a person who is not interested in real love. That’s ok if what you want is a booty call, but swipe left if you want more.
3. For me, the years have been a process of self-discovery. What things have you learned about yourself that you are proud of or pleased with? What have you discovered about yourself that you had to work on? What have you discovered recently that needs work/you are working on?
RoM: For a relationship to thrive, partners have to grow together, or they will grow apart. Asking this intense question may be too much for a first date but if you send it in a text or email and give a person time to think about it, you will have saved yourself years (if not a lifetime) of carrying the dead weight of a person who is neither interested nor capable of positive relationship growth.
4. The process of learning & education are important to me. I am a lifelong learner. If you had another 60 years to live, what would you want to learn about? Tell me some of the things you’ve learned in the past year?
RoM: A lot like #3, this question tells you whether a person is capable of growth through learning. The curiosity to learn about the world around us is necessary for growth and improvement. A person who thinks they’ve already learned enough for one lifetime is a person who is so set in their ways that you will only ever be a hood ornament in their pre-planned future, never an equal partner.
5. I’ve discovered that money is a philosophy, if people’s philosophies mesh, it can minimize money quarrels. What sort of money philosophy did you grow up with? How has your personal $ philosophy changed over the years? What words of wisdom would you give a young person about money?
RoM: Financial troubles have spelled the downfall of many an LTR. This question is not so much about looking for red flags as it is an opportunity to start a conversation that will lead to growing together in this vital area. What you’re looking for is a person with enough mental flexibility to change their paradigm. A person who responds, “Money is X.Y. & Z.” in no uncertain terms, is a person who is likely to be controlling and tight-fisted when it comes to money & may destroy a good relationship rather than destroy (or even question) that paradigm.
6. I have learned a lot about love from raising my children. What have you learned about love? How do you apply that learning now?
RoM: One of the things my children taught me is that love is what you DO, not what you feel. There are times when you won’t feel loving but you’ll still choose to DO the right thing to support your child’s (or relationship’s) future well-being. Another thing they taught me is that ‘like’ is just as essential as love. You can love people (like toxic parents) without liking them much. But to have a happy home life you need to like the people you live with. Likewise, there may be times and situations when you glimpse an aspect of the person you love that turns you off. You still love them, but you don’t particularly LIKE that aspect. This question provides an opportunity to discuss and explore love without making it awkward and before you get in too deep. As a baseline, a person who cannot talk about love has never experienced love, and may not be capable of love.
7. I have studied relationships and really worked on the skills needed for a solid, happy relationship myself. What would you say is needed to make a live-in LTR work? What strengths do you bring to the table in terms of relationships? What are some things you’d still like to work on?
RoM: This is a pretty direct question, and one you may be tempted to wait on until you are committed to the relationship. Don’t wait. Ask this one early and often to save yourself heartache and grief, not to mention wasted years. If they aren’t willing to think and talk about what makes an LTR work, they are not really interested in an LTR. There are a lot of people who live in the fantasy world of movies and songs thinking that finding the right person will magically make life perfect without really trying. It’s the “happily ever after” syndrome. It is a toxic mindset that will destroy marriages. Nothing good works without an effort.
8. I’ve discovered some basic differences between men and women, even though each person is unique. What qualities & strengths do you admire in women? What qualities & strengths do you admire in men?
RoM: This is a question to root out misogyny or misanthropy. If your potential date cannot name a good list of general qualities of your gender, they are not prepared to appreciate YOUR qualities, plain and simple. At the same time, if your person is quick to name lofty or stereotypical qualities that you (or most of your gender) don’t naturally possess (like, say, cooking or cleaning) they are a controlling person who wants you to meet their fantastical demands, and not a realistic partner.
If you like the questions as written, go ahead and use them. If you would like to rewrite the questions to suit yourself, use the RoM breakdown of what is being asked and what can be discovered as a guide. Ideally, you would be asking these questions by text/email before you even meet for that first coffee date. Otherwise, you will find yourself on the receiving end of the intense romantic seduction (brainwashing) that toxic people like to aim at their next victim. Each time you rule someone out, think of all the pain and heartache you’ve saved yourself. And remember you don’t need a big group of people interested in you, you just need one really good person, who suits you and genuinely wants a good relationship.
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