Convo-Tip #1: Acknowledge awkwardness but go forward anyway

If you’re chatting with a friend and want to delve past the formalities of weather, sports, and kittens, you’ll need a transition. Deep, meaningful conversations are what we crave but getting to them can feel awkward. Most of the time, that awkwardness keeps us out of deep conversations.

One direct way to get through that awkwardness is to straight up acknowledge it. Say it out loud.

Say, “I feel a little awkward even bringing this up, but…”

And BAM! You’re in.

By telling your friend you feel awkward, you’re letting your guard down, taking advantage of the Opening Principle.

At the same time, though, you’re also creating some expectation, some tension. When your friend hears that this feels awkward for you, your friend will start bracing for it. That’s good because no matter what you share, your friend’ll probably feel relieved.

I’m complicating this a little bit. In practice, this all happens in a matter of seconds, so it’s fairly unconscious on your friend’s part. Still, both those dynamics are present, the Opening Principle and the awkward expectation followed by the “not as awkward as I thought it would be” resolve.

Warning: If the resolve isn’t fast enough, this fails

You can botch this two ways.

1.You can never resolve it. One person I know seems to enjoy pointing out awkward situations. Trouble is, he points them out but rarely does anything else to help them. That’s not cool.

Contrary to what that person might think, simply pointing out awkward situations isn’t enough to dissolve them.

2. You can keep the tension in the air by drawing out the resolve. “I feel a little awkward even bringing this up, but do you mind if I ask you anyway? …Okay? Okay, and if you’re not comfortable with it just tell me to stop at any time… please. All right, here’s the thing…”

Sheesh, if you add all that filler, you’ve killed it. By then, it’s just an awkward situation. It needs to stay punchy: “I feel a little awkward even bringing this up, but… what do you value most in your spouse?”

Keep the tension short. If you must add disclaimers, add them after you’ve released the tension by asking the question or sharing the information first.

Overall, the “awkward” topic doesn’t even need to be awkward, just something slightly deeper than the average, superficial chatter. Make the transition quick and dive into the deep end of the conversation. Once you have it down, you can easily jump into almost any topic in only a couple minutes.

Serving Suggestions:

(1) Start a conversation with someone today, someone you might not have otherwise chatted with today.

(2) Take the conversation deeper – if only slightly deeper – within two or three minutes by using this phrase (or something similar): “I feel a little awkward even bringing this up, but…”