Why You Keep Putting Off Texting or Asking Out a Woman You Like, and How to Stop

You put it off because a no feels worse than not knowing, so you wait until you feel ready or until the timing is perfect. That moment never shows up. The fix is to make the ask small, draft it now, decide ahead of time how you'll handle a no, and send it at a time you've set.

The solvingprocrastination.com article on fear describes fear as a powerful emotional deterrent. Putting the task off gives you quick relief, but it usually makes things worse over time, because the fear grows and guilt or shame can follow. The fears behind delay include fear of rejection, fear of negative evaluation and fear of regret.

The two feed each other. The article describes a cycle where putting things off makes the feared outcome more likely, which makes the fear bigger.

You're not alone in it. A writer who asked eight men why they don't ask women out wrote that fear of rejection and lack of self-confidence were the main reasons.

There's a second version of this that sounds more reasonable: "I'll start when I'm in the right mood." That mood is unreliable. If you build your life around motivation, your life will have the consistency of a cheap folding chair. Discipline works because it removes the negotiation. You stop asking, "Do I feel like it?" and start asking, "Is this what I do?"

The solvingprocrastination.com article on fear recommends starting with a tiny step and giving yourself permission to stop there. It also suggests doing the preparation first, like filling out a job application without sending it, so the final action takes one step.

For texting a woman, that means:

1. Open your messages and type her name.
2. Write the text. Don't send it.
3. Save it, then set a time to send it.

Here are some plain texts you can adapt:

• After meeting: "Good talking to you Tuesday. Want to grab coffee Saturday afternoon?"
• After chatting for a while on an app: "I'm enjoying this. Want to get a drink this week instead of texting back and forth? Thursday or Saturday?"
• For someone you see at the gym or a class: "Hey, it's the guy from the Thursday class. Want to get coffee after next week's session?"

A specific day and place gives her something easy to say yes or no to. "We should hang out sometime" gives her nothing to answer.

The same article recommends planning how you'll cope with a no before you send the text. Write it down in one line: "If she says no, I reply 'No problem, take care' and go to the gym."

That also gives you a pause button. You don't need to send a dramatic message at 1:12 a.m., or double-text five times like you're filing a missing persons report. You can wait, think and answer like a grown man.

If she doesn't answer, send nothing else. A single no, or no reply, doesn't tell you anything about you.

The article also suggests listing the costs of letting fear decide, and the benefits of acting. Do it in two columns, with one honest line each:

• If I don't send it: I still don't know, I'm still thinking about her next week, and the same thing happens with the next woman.
• If I send it: I get a yes, or I get a no and I'm free to move on.

In a Psychology Today column, Harriet Lerner argues that the problem is you don't have enough experience with rejection, so the fear stays big. Her "one day cure" assigns the person a rejection target for one day, and she once gave a client 75. He was to ask women at a coffee shop and at the foot of a bookstore escalator, using a short scripted invitation to coffee.

It didn't go as planned. Several women said yes. His motivation dropped, and he called a coworker instead, who had started seeing someone and declined. Several days later, he asked out a neighbor he'd chatted with, and they've been dating since. He never used the script.

You don't need the full version. A smaller one works on the same idea: start with low-stakes asks, like inviting a friend to a game or a coworker to lunch, and work up. Use good judgment about when someone isn't interested, and move on if she isn't.

Put the send time on your calendar the way you'd put a gym session there. Decide in advance what "non-negotiable" means for you. For example:

• Texts you've drafted get sent at the time you set, not "when it feels right."
• No checking dating apps during work hours, and no late-night impulse texting after drinks.
• A weekly cap on app time, so you don't spend two hours "just looking."

Ask a friend to check in at the send time. The article on fear suggests getting a friend to be with you or check in when it's time to act.

Look at which fear is behind it. Is it that she says no, that she says yes and you have to follow through, or that you'll look foolish? Write down what you fear and why it may be exaggerated, then keep the list for next time. If the stalling is severe and touches the rest of your life, a therapist can help.

You don't have to feel brave. Send the text you already wrote.