On a great date, the conversation will flow, there will be a bunch of questions you want to ask and a bunch of topics you want to pursue, and it will end with a continued sense of fascination about the person with whom you’ve been spending time.
Most dates aren’t great dates.
But before we start talking about my own personal date conversation dislikes, let me suggest that we all try our best not to take this post too seriously. Because you know, life is short and we’ve all made a few of the conversational blunders I’m about to point out. ME TOO. That doesn’t mean they aren’t funny or worth talking about. That also doesn’t mean you fail at dating or socializing.
It simply means, hey, life is ridiculous sometimes. We screw up sometimes. Things that don’t work for me might work swimmingly for you. Etc., etc.
So with that out of the way, let’s talk about my least favorite conversational gambit of all time: the What Do You Like to Do in Your Spare Time question.
Sometimes this question can masquerade as “What are your hobbies?” Both questions are about equally wretched and boring. In fact, I hate this question so much that at this point I will endeavor to avoid having to answer it. Unfortunately, most people who have strayed so far off a good conversational path will inevitably HOLD THEIR GROUND, thereby consigning us both to an asinine few minutes. The only consolation, and it is a tiny one, is that I can then ask them the same bad question to see if they actually have a good answer to it. For science. (But they don’t. They never do. At least not so far.)
Okay, stop and take a deep breath if you often ask this question. I’ve asked it too. We are okay. Really. Just, you know, maybe think about it before you ask it next time.
Here’s why I think it’s such a bad question: because the response it encourages is merely a bland list of activities. Basically this question sucks for the same reason that my blog sometimes sucks, because it doesn’t give you nice, juicy concrete details. It doesn’t lead to stories. It doesn’t lead to connection. It leads to boring boring boring. (Or if you’re talking to me, it leads to me going completely blank and giving you a piteous look.)
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A better conversational tactic is to talk about what the two of you have been doing recently, which will usually automatically give rise to talk about activities and subjects that interest both of you, but in such a way as to encourage anecdotes and details and maybe even an actual discussion. (I know, I know, I set my sights high.) Granted, if all you’ve been doing lately is working, this won’t be as effective, but here, have a nice reason to strive for a little bit of balance in life. You’re welcome. (Or, barring that, I suppose you could talk about what you want to be doing or what you’re going to do.)
Here are some other quality conversational blunders I love to hate:
- “I know you don’t drink alcohol, so let me talk for a lengthy period of time about alcohol.” No. Just don’t do it. In a group, I will deal with it. One-on-one, this is totally unnecessary. If you have a huge passion for wine, or Scotch, or whatever, I accept that maybe someday I’ll have to listen to you talk a lot about it, just as you’ll have to listen to me blather about musical theater. But that time is not the first date. Or the second. Or probably even the third. Basically it just shows you’re not paying attention to what your companion finds interesting. (If, on the other hand, it hasn’t come up that I don’t drink, you’re totally off the hook. Expecting your date to be a mind-reader is not cool.)
- Personal questions about money. I understand my date might want to be reassured that I’m solvent and responsible and not about to flee the country or file for bankruptcy, but beyond that, waiting a couple dates before prying into all the details of my financial situation is a good call. I know some people think this is totally fine behavior, which is their prerogative, but I’d never to do it on the first couple of dates myself.
- “Here’s what you should do about x situation that you didn’t ask for advice about.” Ugh. This is often kind of annoying anyway because people usually want a different response (and that’s if they’re actively talking about their problems in the first place, which is rarely the case in early dating, when you’re merely trying to get to know one another). But on the first couple of dates, it’s particularly bad because the other person probably doesn’t even know enough details or information to actually be giving relevant advice. But then when I stand my ground and then try to change the subject, they won’t always let it go. Fun times.
- Saying something mean-spirited/putting the other person down. Here’s the thing. Maybe the person was nervous. Maybe the person was making a joke (granted, a mean-spirited joke). But ultimately I don’t care why it happened. If someone says something kind of mean during one of your first times together, odds are it’s going to happen again. And again. And again. This isn’t just a red flag, it’s a get-the-hell-out-NOW flashing neon sign of doom.
(Note: I’ve gotten some push-back in the past when I’ve talked about this particular neon sign, and I think it might be because people are worried their teasing will be interpreted as mean or negging or whatever. But if it is interpreted that way, then that means the two of you are not compatible, end of story. Your senses of humor simply do not mesh. Or else it means you are crossing the boundary between teasing and being disrespectful and aren’t aware of it. But nobody owes you a lesson in that; it’s something you’ll have to work out for yourself. Or maybe people are worried that I am too sensitive. Don’t be. My main failure at reading people is sugarcoating what I know and being too accommodating, and I’m fine with being willing to stand up for myself.)
In conclusion, most dates aren’t amazing out-of-this-world I-can’t-stop-talking-about-it dates. If they were, dating would be a simple and short process (and for the people for whom it is, hey, more power to you!) But dates are certainly a lot more pleasant when both people are kind and polite and make an effort to be in tune with one another. On that I suspect we can all agree.
PS: If you would like to share your least favorite conversational gambit of all time, I’d love to hear it!
The Practical Free Spirit 
First, this: “My main failure at reading people is sugarcoating what I know and being too accommodating”. I feel you. I really, really do. I’m learning the value of standing up for myself, too. And not down the line when crappy behavior has gone on for a while, but right at the start of it. Which is really hard! But so worth the effort.
Second: I hate being asked what I do. This is always a question about what I do *for work*, but it’s never phrased like that. I *do* a lot of things, and my paycheck gig is really the least important of them. I think it indicates our culture’s habit of defining people by their jobs, which I find to be so limiting. Especially when I’m just in a position as a way to fuel my passions, and not because I’m passionate about the work itself.
On the contrary, I love to ask people about their job because I find it insightful. Do they like their work? Do they have nothing but bad to say about their coworkers? Is it a job or a career? Does their job define them or is it just something they do? Are they unemployed and if so how does that make them feel? Is their job exploitative? Do they aspire to more?
Yeah, I try to avoid the “what do you do” question at parties and the like because I know a lot of people don’t like that question. In dating I find it usually just comes up on its own, which is interesting.
I am lucky in that I don’t mind that question at all, but that’s only because my career and one of my passions happen to be the same. When I worked in marketing, it was a completely different story! 🙂
“I know you don’t drink alcohol, so let me talk for a lengthy period of time about alcohol.”
Subtopic I get a lot: I know you don’t drink alcohol, so let me talk for a lengthy time about how I don’t drink all, don’t drink for the last 37 days, plan to quit soon, thought about quitting in the past, my own personal philosophy about how to quit and why the dominant quitting paradigm is not for me, etc.
I don’t drink, but I don’t want to hear someone else’s personal trials and tribulations with not drinking. I’d be in an AA meeting if I wanted to hear that.
One topic I do like asking on early date: What are you passionate about? Here’s what I’m passionate about!
Yeah, I tend to like that phrasing better myself. In my experience, it is both broader, opening the field to ideas and beliefs as well as hobbies, and it narrows things down so you can go deeper as well.
Along those lines I would ask, “What’s the coolest thing you’ve ever done?”
I use that question when interviewing job applicants, but focused on programming. They probably don’t know it, but it’s the most important question I ask. A little because of the details they give, but mostly I’m looking for a spark of passion.
YES! I would love to ask this, and I would love to be asked this. I hope this question becomes a classic in my conversational repertoire.
Completely unrelated to dating but maybe not…
I’ve hosted a lot of group events (large and small) with folks who may not know each other well or at all. One of my favourite questions is always, “What’s the worst job you’ve ever had?” This one almost always leads to funny stories (most people have had at least one horrifically bad job) and spins the conversation off into all kinds of interesting directions. Plus you can learn a surprising amount of information about a person with this question.
I love this question! I’m going to try to remember to bring it out sometime.
“What do you do for fun?” is a question I find quite useful, especially on dates. It is a gateway to what they are passionate about. It also gives ideas for future dates. It opens up related questions:
You like to watch movies? What kind?
You like to read? What kind of books? Did you read Twilight or 50 Shades?
You like concerts? What are your favorite bands?
I’m not familiar with that hobby; tell me more about it.
You like travel? What is the favorite place you’ve been?
Oh Josh, if only everyone followed up on that question like you do, everything would be better. EVERYTHING. 🙂
“Personal questions about money.” I love to hate this one, as someone asked me, after noticing I was in an angora coat if I “just like to spend money.” What a butt lunch, and then he proceeded to right in front of me, spend three times the amount on a pair of tailored trousers. For real, now?
I like to ask people “What gives you joy?” The usual response is a double-take followed by a thoughtful look followed (most of the time) with some things you might never hear otherwise until much later in the relationship.
And if not, well, there’s your red flag.
A friend taught me these two, which I like (one of them is basically Dave Trowbridge’s, above): “What is bringing joy into your life right now?” and “What are the challenges you are facing?” Then you learn what people care about, whether they are embracing something and/or pushing against something, and how they handle both. Also, you can tell whether they they are the type to stay in the moment and/or are optimists or pessimists based on what they say and how long they spend answering each. I hate the “What do you do for fun” question. And I hate when people spend awhile defending their use of drugs. I don’t use anything, and I have come up with a one sentence pat answer when people inevitably ask me why not. I try to keep it short so as not to create much divide early on. Good luck, Everyone!
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