Five Ways to Skip the Small Talk

I’m impressed by the vast amount of restraint I exercised in getting through the first date with my now-husband without coming out with it, “If it’s ok with you, I’m going to end the niceties and have us start telling the absolute truth of it. Shall we?” 

So dutifully patient, I waited a few solid minutes into our second date. 

Conversation 2.0, both the platonic and nonplatonic-oriented kind, is sometimes hard to make the leap to, especially in a world where the niceties of shallow small talk sometimes feel like the only space that is safe. 

So, you’re up for it, you are willing to take the risk in order to glean richer conversation. What is the least abrupt and startling and most organic and graceful manner in which to do it?

Here are my five suggestions:

1)    Evaluate the interest level

We all start with basic small talk in the beginning and ought to. If we have properly functioning sonar, we will get signals about just how comfortable the other person is with the invitation into Conversation 2.0. 

If you get frosted trying to transition, one of two things is happening. Possibly the person is deeply introverted, just as you may be and, even though they in fact would appreciate deeper conversation, just cannot find the right frequency to communicate that. It’s easy for our sonars to confuse discomfort for disinterest, so don’t give up prematurely. 

The second thing that might be happening is a full-on, bonified ice-out. If you find yourself bearing most of the conversational weight and you hear the ticks of some far-away clock filling gaping awkward silences and you could swear that they are, inch by inch, shuffling their bodies (maybe complete families) away from you, there’s a serious chance they’re simply not available or interested.  

In any case, you can say you gave it a fair shake. Aborting when the signs are pointing to it is not losing; it’s acknowledging that this particular match-up is not in the cards. Shuffle on over to someone else.

2)    Ask lots of higher-level questions. 

Have you ever been befuddled over why you are not getting anywhere with a person who you would like to know better? All the signs seem to be there: common interests abound, signals are there that the feeling is mutual, you’ve not once found yourself deeply annoyed at her, and there’re big enough portals through the vague where you can see the magic and make you want more. But, the level of conversation isn’t consistently breaking through. 

Could it be that conversation isn’t evolving in the direction you want because the quality of your questions isn’t taking it there? There is nothing wrong with low-level small talk questions, especially when there are no signs of investment. But when it’s clear you’re both trying, experiment with the higher-level ones.

Low-level          High-level questions

How are you?   On a scale of 1-10, 1 being the lowest of lows and 10 being

the highest of highs, how are you?        

How was your wkd?  Tell me something awesome and something not so

awesome about your weekend.

How was your day?   Tell me one interesting thing about your day.

Is the family well?    What’s up with Janey? Biggest challenge parenting her right

now? And Joey? What keeps you up at night with him?

How about this weather?   I’m wondering what you think about God.*

*Mainly joking here. Busting out God talk may come easier for some than others, but it almost never is a fitting replacement for weather talk. Talk about weather while standing in the rain at school pickup. Maybe find a quiet corner of a coffee shop for God. 

3)    Laugh A lot

I’m not asking you to fake it here, just not to forget about it.  

I don’t know about you, but conversational brilliance is laborious for me… I’m interesting and delightful and curious but it takes work to show it. I’m usually cognitively peddling hard to will my sense of humor forward in the form of clever wit here and there while filtering out all the unnecessary things that come to my mind that don’t matter in the conversation while listening intently with hopes of retaining a thing or two that comes out of their mouths while remembering that good conversation requires healthy back and forth – don’t get too lopsided! – while not getting killed by the ball blasting toward me on the sidelines of a soccer game. That’s A LOT of demanding work. My point is this: Take a breather from time to time to recognize that she’s working hard, too, and to reward her work with an appreciative chuckle or giggle when she shares something interesting or funny. I’ve found that laughter brings our guards down and reserves cushy room around the firing away of our questions and stories for a healthy breath to live in the conversation. Plus, stopping to laugh gives us a break from all that thinking. 

4)    “I’m thinking about what you just said, which was really great, and this is where my brain is going with it…”

Story swapping is fine, but sometimes I find that we forget the glue. Without a transition that honors what the person just said, smacking on another story to the layer beneath it can mistakenly come across as one-up-woman-ship (or the other way: one-down-woman-ship). Remember to pause for that moment of acknowledgment and note what it was about what they said that spurred on something else in you. 

5)    Advance beyond the quickies and set up a (standing) date

Finally! You’ve really rocked Conversation 1.0 during the short intervals of time at gymnastics drop off or after barre class or on the basketball court sidelines. Congratulations! Now it’s time for some courage: You’ve got to ask her out on a date. Three-minute exchanges are great, but, even with kick-butt high-level questions, the nature of filler time just doesn’t invite depth or intentionality. It’s time to dedicate some time to just the two of you. Filter through the hobbies you have in common and pick one to do while conversating (Walking? Running? Knitting? Thrift-store shopping? Volunteering? Basket-weaving?). You’re on your way to a less-than-surface-level friendship! And, when you’re sure, make those dates standing ones. This offers a built-in reminder to keep the momentum going!