Flirting: 10 Common Concerns
Estimated reading time: 5 minutes
So, you read Part 1 and understand that flirting doesn’t have to be creepy or performance art. And perhaps you even challenged yourself by smiling at someone a second longer last week.
But… it still feels awkward / weird / uncomfortable.
You’re on the right track!
“If it scares you, it might be a good thing to try.”
You may be tempted to hide when it comes to flirting, too.
Two Blockers: Fear and Lack
I’m going to assume that you’re like most people and you want to flirt, but hesitate.
Why? Usually, it comes down to one of two things (or both):
Fear of being misread, rejected, or feeling embarrassed
Lack of clarity, confidence, or experience
Let’s walk through some of the most common concerns and see what might be driving them.
Common Concerns About Flirting
“I don’t know how to flirt.”
→ Driven by a lack of knowledge or skill.
No one teaches this stuff. If you only associate flirting with smooth lines or swagger, it’s easy to assume you’re just “bad at it.”“I don’t want to come across as creepy.”
→ Driven by fear of judgment or making someone uncomfortable. Especially for people who are respectful and thoughtful, the risk of being misunderstood can feel too high.“I overthink everything I say or do.”
→ Driven by fear of rejection and social anxiety.
When flirting feels performative, the stakes start to increase. You may second-guess tiny, inconsequential things.“I can’t tell if someone’s flirting back.”
→ Driven by lack of experience reading social cues.
Most flirting is subtle and if you’re looking for something obvious, you might miss what’s actually happening.“I freeze or go blank in the moment.”
→ Driven by performance anxiety.
You want to say something clever, but your brain short-circuits under pressure.“Flirting feels fake or manipulative.”
→ Driven by discomfort with performativity.
Some people equate flirting with playing games, especially if their idea comes from flirting as Casanovas and Lotharios.“I’ve flirted before and it didn’t go well.”
→ Driven by fear of past failure.
A single awkward experience (or a particularly painful one) can shut down your willingness to try again.“I don’t want to lead someone on.”
→ Driven by fear of sending mixed signals.
Especially if you’re unsure about your interest level, flirting can feel risky or even irresponsible.“Is it even worth the effort?”
→ Driven by burnout, disillusionment, or low self-confidence.
If you’ve been single a long time or had a string of disappointments, the idea of being playful might feel pointless or exhausting.“What if they take it the wrong way?”
→ Driven by fear of misinterpretation and unintended consequences.
You meant it as playful, but now you’re worried it could be read as too forward, too intense, or even offensive. This concern often comes from wanting to be respectful and liked, but it can lead to over-censoring or avoiding flirting altogether.
Final Thoughts
I’m not listing these concerns to diagnose or fix you. Only to remind you that:
These are all incredibly common.
There are different ways to respond to fear and discomfort.
If anything, they’re signs you care about how you come across. You’re thinking about consent, mutual interest, and connection, not just pushing your agenda.
Flirting doesn’t require you to become someone you’re not, but it might require you to stretch a little. That is, risk occasionally being awkward.
“The secret to being wrong isn’t to avoid being wrong. The secret is being willing to be wrong.”
If you don’t know where to start, start by noticing which concern is prevalent for you. That’s where your experiment begins.
What’s Next
Sometimes flirting flops. So, what can you do about it?
Now that we’ve covered what stops you from flirting, what happens if you do try to flirt and it flops?
Stay tuned for the next article! We’ll look at what to do when the moment feels awkward, confusing, or just plain off… and how to bounce back without spiraling.
Want to know when the article is published? Join the Insiders List
