Why Has It Become So Awkward to Initiate Friendships?

Consider, if you will, these three different scenarios that have all taken place in my life recently:

1. A man asked if I would have dinner with him. Before I could even think about my response, he quickly added, “But if not, that’s okay. I asked another girl out a few weeks ago and she said yes but then she didn’t show up.”
2. A woman I share mutual acquaintances with hesitantly asked, “Would you ever want to hang out sometime? If you don’t, that’s totally fine though. I get it.”
3. After chatting with a gal at church I seemed to have a lot in common with, I asked if she wanted to meet for coffee sometime. She said yes but was noncommittal and slow to respond in subsequent conversations. After several weeks, I gave up on coffee and felt awkward for ever asking.

Whether with potential dates or potential friends, all these encounters felt eerily similar, because they all felt awkward, and in each one, someone was risking rejection – and was very aware of it.

I’ve been on both sides of the equation, so I empathize with every awkward asker and every awkward askee. I can’t help but wonder…when did it become just as intimidating to try and make a friend as it is to try and get a date? Why do these encounters feel like one and the same in 2023?

How did we get here?

Is COVID responsible for this? I don’t think so, because I experienced these weird encounters before the world shut down, although I do think lockdowns made things worse.

Is this the result of online dating and social media? Are people so unused to face-to-face interactions because apps make things too easy? Are people too accustomed to swiping left in hopes of someone “better”? Is everyone so used to being swiped left on that the spirit of rejection has completely taken over?

I don’t know. I just know that something is wrong when we can’t even extend an invitation to a potential friend these days without feeling insecure and fearing rejection.

It’s awkward! It’s awkward being asked to do something with someone who is clearly afraid you’ll say no. It’s awkward to ask someone you think you’re connecting with to hang out and quickly realize you weren’t on the same page like you hoped.

When on earth did making friends become so awkward? And what’s the solution?

Personally, I think most of us need to spend a little less time in the digital world and a little more time surrounded by actual humans in real life. We need more places we can meet people that aren’t online.

Someone has to be the assertive one

These awkward friendship scenarios also beg the question: where’s the line between assertiveness and desperation? I mean, someone has to make the first move if you’re ever going to make a friend. I’ve talked before about how, for many years, I just waited for extroverts to adopt me. I never initiated any friendships; I just accepted whatever friendships came my way…until they stopped coming my way and I had to learn how to step out and befriend people on my own. But even after years of being more assertive, I still often wonder: Did I come on too strong? Was I too direct, or was it too soon? Should I have friended them on social media first? Did I come across as weird?

All these thoughts bombard my brain, but then the realistic part of me also argues: All you did was ask someone to coffee! You don’t know when you would’ve run into her again. How else are you supposed to make a new friend?!

The truth is, just as in dating, you win some and you lose some when it comes to making friends. You strike out sometimes. And you usually don’t know where the elusive “line” is until you cross it. (Or maybe it’s just me crossing lines like I’m wearing the alcohol impairment goggles in driver’s ed.)

I wish I knew all the right answers and the right formulas, and you probably wish you knew, too. It’s a new season and most of us are feeling the tension of the shifting and sifting of relationships that always comes with it.

My encouragement to you today is simply to not throw in the towel. We all need good friends, and you could be the good friend someone else needs in this season, not to mention you stand to gain a wonderful new friend for your own benefit, as well! Take the risk. Read the situation as best you can, and then seize the opportunity you have to ask someone to hang out. (Or, if we’re talking dating, to go out on a date – do not cop out and use the terminology “hang out” unless you want to confuse someone about your intentions.)

Remember, many people say no because of their own social anxiety, not because they mean to reject you. Be the person who is willing to “adopt” others and ask, even though you sometimes get a no. You will probably be appreciated and admired for your assertiveness more than you think.

Oh and, this goes without saying, but it never hurts to consult God on what he thinks you should do! I often pray, “Lord, help me to speak up when I need to speak up and shut up when I need to shut up!” (It’s still a work in progress. 😬🙊) Whether your Mighty Counselor tells you to go for it or keep your mouth shut, listen to him. It will save you a lot of trouble and point you in the right direction – his direction.

He is your Friend and I pray he brings the right people around you as he simultaneously leads you to the right people! Your people are out there, and I bless you to connect with them in this season.