“What Should I Text Him?” May Be Ruining Your Love Life

How many times have you asked your friends, “What should I text him?”

Or maybe you’ve experienced something along these lines… You type something out, overthink it, delete it, type it again, delete it again… and then throw your phone across the bed because, somehow, no response feels “right.”

Here’s the problem with that “What should I text him?” question: it’s incomplete.

The Hidden “If” Behind Every Question

Usually when we ask, “What should I ___?” there’s an invisible “if” statement attached.

• What should I watch on TV? might really mean What should I watch if I want to relax? Or if I want excitement? Or if I want to learn something new?

• What should I eat? could mean What should I eat if I’m starving? Or if I’m trying to lose weight?

• Where should I go on vacation? might imply Where should I go if I want to recharge?

You get the idea.

But now, with these questions, you – and/or whoever you’re talking to – usually know what the “if” statement is, based on the context.

But when it comes to dating, “What should I text him?” rarely (if ever) has a clear “if” statement – at least not one you’ve chosen on purpose.

Thus, one of two common problems is likely to (unknowingly) occur:

Problem #1: You outsource your “if.”

You ask friends (or the internet) what to say… and then they get to fill in the “if” blank for you. Their version of the “hidden if” might be:

• If you want him to chase you…

• If you don’t want to look desperate…

• If you want him to think you’re fun…

But then what inevitably happens?

Well, you end up dating by their rules, their standards, their values – not your own.

And who exactly is this guy trying to get to know again?

Problem #2: You flood yourself with conflicting “ifs.”

Even if you keep the question to yourself, it’s easy to – again, likely unknowingly – get tangled in all the conditioned “ifs” floating around in your head:

• If I want him to like me…

• If I want to play it cool…

• If I want him to take me seriously…

• If I want him to ask me out…

Most of these “ifs” have two things in common:

1. They’re focused on gaining his approval rather than expressing your truth.
2. They leave you feeling overwhelmed, confused, uneasy, anxious, and/or insecure. Yeah, not fun.

The Only Valid “If”

In my opinion, the only version of this question that actually makes sense is:

“What should I text him if I want him to know the real me?”

Okay, so now that’s a great question. But only you can answer it – not your friends, not the internet, not even ChatGPT (no matter how “close” you two have gotten!)

Because no one else knows what you genuinely want to say.

Better Questions to Ask Yourself

So, instead of chasing the perfect answer to a poor question, how about flipping the question entirely?:

• What do I actually want to say?

• How do I feel about this?

• What would be fun, honest, or interesting to ask?

These questions lead to more natural conversations, fewer headaches, and a love life that actually feels like yours (and not like an endless group project).

Stop Trying to “Get It Right”

So, that’s my beef with the simple question, “What should I text him?”

It seems harmless, but it’s representative of a much larger problem when it comes to dating: the desire to always “get it right.” And I strongly believe that part of what makes dating so stressful is the pressure to get it “right.”

Meanwhile, there’s so much freedom, joy, exploration, fun, and opportunity in releasing any idea of “right” and “wrong” – especially in regards to expressing yourself, asking curious questions, and sharing who you authentically are with someone you’re trying to get to know (and who’s hopefully trying to get to know you back!).

Whatever internal question you ponder, whatever external inquiry you pose, and whatever you end up saying, make sure it’s coming from within because a life of emotional ease and fewer matches is better than a life of people “accepting” you for the play-pretend version of yourself.

Love,

Imani

If this resonated, here’s more.
Little questions like these are often hidden behind sneaky rules (societal standards, familial conditioning, arbitrary dating advice, etc.) that might be holding you back without you realizing it.

If you’re ready to let go of outdated dating advice and start connecting with more confidence and clarity…

 Download this free guide now: 12 Rules to Reconsider Before the First Date
It’s scrollable, skimmable, and surprisingly freeing.