Who Should Chase Whom in Dating?

There seems to be some confusion surrounding who should be the pursuer when you’re dating at this stage of life. Men love women who make the first move, and many women love the feeling of being pursued. So how do you meld these two concepts?

Make the First Move

One of the main reasons men love women to make the first move is that they are deathly afraid of rejection. This is something that men have been dealing with since puberty, and they want to avoid at all costs. So much that in some cases it keeps them from taking any type of action at all.

Women always set the pace of the relationship and once you understand men’s fear, you can create an experience that will be a win-win for both of you, and it’s not that difficult to do.

So many of my female clients tell me they are tired of driving the bus by themselves. They are looking for a man with a plan so they can lean back and have more fun. They did all the planning when they were younger, and they want someone with whom to share this responsibility now.

I totally get it and feel the same way. It’s a good rule of thumb too, because once you take control of a relationship, it’s almost impossible to give it back. If you start managing your dates at the beginning, you’ll be managing your dates throughout your entire relationship should one develop.

Read more: Understanding Compatibility in Early Dating: What Really Matters.

The Choice Is Yours

So how can you lean back, which is feminine energy, by the way, and still be the first one to reach out? It’s not as complicated as you may think.

It doesn’t matter if you’re dating online or meeting men in real life, you can still make the first move without taking control of the relationship by simply creating an opportunity for the man to step up. Now that you know how serious men feel about rejection, you know you could be waiting a long time if you wait for him to approach you. I almost always reach out first when I’m dating online.

I empower my clients so they feel comfortable doing the ‘picking’ rather than wait around to be ‘picked’ by a man who may or may not be a good fit for them. When you do the picking, you get to choose who you invite into your world, and it saves you time and frustration.

But Let Him Plan

The way I teach my clients to do this is simply to show their interest, and then lean back and let the man plan the date. This is what it sounds like when you’re texting or talking on the phone.

“Bob, it’s been great texting with you, and I feel like you’re someone I’d like to talk to. I’m happy to send you my number, what do you think?”

“I’ve really enjoyed chatting with you tonight and love that we have so many things in common. I’d be interested in learning more about you over a cup of coffee. How does that sound to you?”

These simple statements show him you’re interested and eliminate his fear of rejection while they volley the next steps back to him. Once he says, “Sure,” then you can simply tell him what days you’re available and ask him to pick a time and place to meet.

If he has trouble coming up with a location, some women offer a couple of options while other women simply tell them nicely to figure it out. If you give him options, you still want to want to leave the final decisions and planning up to him.

“I like ____, ____ or _____ and I’ll leave in your hands to pick the best place.”

Again, you’re creating the opportunity for him to take the lead. If you like being responsible for everything, you would probably simply give him a time and place to meet. This may be a little off-putting for him if he’s a masculine energy man. This type of man likes having a job to do and may feel a little out-of-sync as a result.

Read more: What Do Single Men Over 60 Really Want? This Dating Coach’s Advice Will Surprise You!(Video)

What if He’s Not Taking the Lead?

So, you made the first move. You showed interest, sent the message, or suggested meeting for coffee. But now… crickets. Or maybe he responded, but he’s vague about making plans, keeps postponing, or always puts the ball back in your court.

This is where it’s important to notice the difference between someone who’s just shy and someone who isn’t that interested – or isn’t ready to date. If a man is genuinely interested, he’ll find a way to follow through. He might need a little nudge at first, but he won’t leave all the planning to you every time.

If you find yourself chasing him down to get anything on the calendar or constantly trying to keep the conversation going, it might be time to step back. You’re looking for a partner, not another project.

Give it a little space. If he picks up the thread and starts putting in some effort, great. If not, you have your answer. Sometimes letting go of lukewarm interest clears the path for someone who’s actually ready to show up.

Read more:The 5 Types You Should Never Date.

This Is Our Time

This is a beautiful chapter of life. We’re old enough to know what we want, and confident enough to ask for it. This is an empowering time, but it does come with some responsibility. We do need to be considerate of the men we invite in our lives. They are much more romantic and sensitive than we’ve been led to believe and words do matter.

If you want more step-by-step coaching so you can date with clarity and confidence, check out
The Perfect Dating Guide for Women over 50.

Read more: How to Date Differently in 2025 So You Can Find Love.

Editor’s Note: Article updated by Sixty & Me.

Let’s Have a Conversation:

Do you approach men first, or do you prefer to be chased? If you make the first move, what do you say? How has this strategy worked for you?