Gaining Confidence in Dating
If you don’t know, I recently moved to Switzerland with my family. And yet, despite my 706-day streak on Duolingo, I still couldn’t speak German. So I knew I had to buckle down and do the thing I hate most: learn German.
It’s complicated. It’s weird. And it’s complex. I constantly judge myself: how bad I am at it, how much further along I “should” be, how embarrassing it feels to have come this far and still feel like I’m nowhere. My brain feels like it keeps running into a wall it can’t climb over.
Whenever I share my frustration, exhaustion, or pain from constantly trying to learn German, I’m met with a flood of advice from native speakers or people who learned it as kids. “You should try X.” “It’s really important that you do Y.” “You have to do ABC.” Their tips are well-meaning, but rarely helpful. They’re based on their own stories, not mine. I don’t have enough time or energy to try them all.
I’ve spent thousands of dollars on classes that build on more classes. I have a stack of papers and books I’ve worked through. And yet my confidence in German feels worse than a first grader’s.
No one really tells you that learning a language is a lot like dating.
It’s a process of learning, step-by-step, how to move through different stages. Some parts come easily, others take a lot of work. It’s messy. You judge yourself for not being as far along as you think you should be. You’re embarrassed because you’re “this old” and your progress feels like it’s back to zero. You get plenty of unsolicited advice on “what you need to do” to get married—or in this case, fluent—and you simply can’t try it all. You may even have a stack of books and resources you’ve poured thousands into, yet still feel like you haven’t gotten anywhere.
I get it. I’ve been in both boats, unfortunately.
Here’s how we move forward.
1) Know that learning is as much about failing as it is succeeding.
You get a date, go on the date, say something awkward, and realize the other person isn’t a good fit. Cool. You learned and got some reps in.
I start a conversation in German, make it a few sentences in, and realize I’m completely out of vocabulary… but they keep talking. It gets awkward and I just want to bail…and sometimes I do. Yes, I failed, but I also got further than before.
2) Remember: you’re developing a skill, not just chasing an outcome.
You’re learning how to communicate, show up on good days and bad, hold boundaries, take up space, and share your needs while also making room for someone else’s. You’re becoming more flexible with plans, more intentional with special moments. You’re building a support team that will help you not just “get fluent” or “get married,” but sustain a great relationship—whether that’s with a person or a language.
3) Balance knowledge and action.
People learn differently: some through books, some through online courses, some through relationships, and some by simply picking it up along the way. (Those learners frustrate me and make me jealous—I am not one of them.) Either way, we’re constantly learning how to communicate better, fix grammar mistakes, apologize differently, and identify the underlying issues—whether they’re emotional or grammatical.
But here’s the hard truth: as much as we like to stay safe and study alone, progress requires risk. You’re going to get things wrong. You’ll ask someone out, or start a conversation, and get turned down. And maybe the next one will turn you down, too. But every time, you’re building resilience. You’re learning the skill. And if you do it with a kind heart and a genuine intent to connect, you can’t really fail.
It comes down to this: confidence comes from proven competence.
Not competence in doing everything perfectly, but in collecting small wins you can build on. You keep learning. You keep adjusting. And over time, those wins stack up.
So focus on micro-goals instead of the big end goal. In dating, that might mean:
Becoming approachable
Getting noticed
Having positive interactions
Going on dates
Getting past the third date
Resolving conflict
Sharing emotional hurts, not just anger
Clarifying expectations
Not bailing when things get serious
Figuring out if someone’s a good fit without idolizing or demonizing them
In language learning, it’s the same idea: celebrate the tiny wins.
Because it’s not knowledge alone—or reaching the final goal—that builds confidence.
It’s showing up. Trying. Learning. Connecting. Adjusting.
And then doing it all again tomorrow.
