5 Reasons Why Women Should Be Bold & Ask Men Out

I’ve come to realize that there are so many missed opportunities out there for singles, especially when it comes to all the single ladies. I know traditionally it has been thought that men always take the lead to ask a girl out and do the whole wining and dining.

But I don’t recommend my clients wait around for that.

In this modern society, I believe it is perfectly fine for a woman to take control of her dating life and let a man know that she is interested. I’ll go over my reasons and hopefully convince you to ask that guy out already.

I, personally, think it shows a confident side of you that makes you way more appealing than sitting on the sidelines and hoping for someone else to take the initiative.

In fact, in 2013, Match.com did a study of 5000 single men and women to see how they feel. And 65% of men actually have been asked out by a woman, and 91% of men answered they are comfortable and wouldn’t mind if women made the first move.

They also felt that women who approached men seemed more confident, which in turn made them more attractive. (Um, that study was done in 2013… we are now in 2025. Come, ladies, let’s keep this momentum going.)

One thing I’ve realized after reviewing tens of thousands of profiles over the years is that most online dating algorithms match you based on your answers to their questions. 

As smart as the technology is, it cannot know your type and chemistry level with each person they offer. That is where the power is in your hands.

 OkCupid.com did a study where they found that women are 2.5x more likely to get a response than men if they initiate.

“If you’re a woman who sends the first message, not only are you more likely to get more responses in general, but you’ll be having conversations with more attractive guys.” — OkCupid

This stat should light the fire to help you start wanting to write men first. I’ve worked with plenty of female clients and helped them make the first move. Yes, it may take some time to find the right match, but I’m here to confirm that these stats are true. Especially the more attractive guys part!

Every time you take the initiative, you are taking control of your love life. Forget leaving it to chance. It takes a lot of strength to prove to yourself that you can handle uncertainty and emotionally be strong through the possibility of rejection.

Most women think this confidence is just in dating, but it is not. It shows up everywhere. By making the first move, you prove to yourself that you are capable of being assertive and expressing your needs.

I’ve had clients who started asking men out and then found themselves speaking up more at work, creating better boundaries in life, and generally advocating for themselves in ways they never had before.

I know the thought of rejection feels so scary. But here’s what I know: men can typically handle rejection more thoughtfully than women expect. Actually, most men I’ve worked with told me that even if they weren’t interested, they were flattered.

They’ll usually say something like, “I’m really flattered, but I’m seeing someone,” or “I think you’re great, but I don’t feel that spark.” And then? Life goes on. No drama, no social media posts, no telling all their friends how “desperate” you are.

Actually, I’ve found that men respect women more after being asked out, regardless of their answer, because it takes courage.

I can’t tell you how many clients have come to me frustrated, wondering why they’re still single. When I dig deeper, I find out they’ve been dropping “hints” to their gym crush for months, or they’ve been waiting for a guy from their friend group to finally make a move.

Here’s the truth. He might be oblivious that you are even interested in him. But just because he isn’t showing interest back doesn’t mean he isn’t interested. He might be clueless.

Men are not mind readers, so if you are interested in someone. I highly recommend that you be direct and tell them how you feel.

What is the worst-case scenario that can happen? You get your answer, and things don’t work out. The best outcome is that you finally have the wonderful relationship you have been desiring.

When you ask a man out, you’re doing him a huge favor. You’re removing the pressure of having to interpret your signals correctly and giving him permission to show interest if he feels it.

I had a client who met her partner at the gym. It was a really simple approach: she came up to him and just started to ask him for advice on how to use a certain machine.

As the days went by, they started to talk more and more, and eventually, she invited him out to have coffee outside the gym. He was ecstatic, and guess what? Two years later, they are now happily married.

So the approach can be simple and direct. You don’t need to be a master communicator or drop hints.  Something like, “I really enjoy talking with you. Would you like to get drinks sometime?”  works perfectly.

Be specific with your invitation. Instead of “We should hang out,” try “Are you free to go to happy hour this weekend?” Give him something concrete to respond to.

If he says no, respond with grace: “No problem, thanks for being honest.” 

Don’t take it personally, don’t analyze what you did wrong, don’t try to convince him. Move on like the confident woman you are.

Honestly, we are living in 2025. You don’t have to sit around waiting for someone to notice you or try to read between the lines to understand the signals being sent. Build up the courage to ask the guy you’re interested in out. You have agency in your love life, use it.

The worst thing that happens is that someone says no. The best thing that happens is you meet your person because you were brave enough to make the first move.