It’s Okay to Ask Where It’s Going—Because the Right Man Already Knows Where He’s Taking You

October 9, 2025

Hi, I'm Jackie

I'm the head cheerleader for your love story, your new 'big sis' and wing woman - so if you're new to me, welcome to me, your love life will be better now. 

When I met my husband, he lived next door. We were friends for four months, neighbors who helped each other with carpooling, kids’ schedules, and everyday life. Neither of us was playing games. I was fresh out of a divorce and still doing my own heart work. But here’s something I’ve learned: You don’t have to be perfect to deserve a love story.

I had grieved my first marriage long before it ended. Some people mourn after a breakup; I mourned while I was still in it. That’s why I don’t judge anyone’s healing timeline, you never know what someone’s walked through.

Back to the story: One day, during a walk, my neighbor confessed that he liked me. We went for coffee. That was our first official date. A few weeks later, we began to see each other through a new lens, one of possibility and purpose.

About two months into dating, six months after first meeting him, I looked him in the eye and said:

“I just want you to know I’m nobody’s girlfriend. I’m a single mom, and I’m not here to date for fun. My girlfriend era is over. So I want to know your intentions.”

Without hesitation, he said,

“I already bought the ring.”

Three months later, he proposed.

That moment taught me something powerful: Men know quickly.

When a man is mature, masculine, and marriage minded, he doesn’t need years to decide if you’re “the one.” He recognizes alignment, peace, and purpose and he moves toward it.

Women are often afraid to ask where a relationship is going because they don’t want to seem pushy or scare a man off. But asking for clarity doesn’t chase away the right man, it filters out the wrong one. Especially if you’re over 35, your time is sacred. You’re not “rushing things.” You’re stewarding your future.

So if you’re reading this wondering whether it’s “too soon” to ask what his intentions are, let me remind you:
You’re not asking for a proposal. You’re asking for clarity.
And clarity is not pressure, it’s protection.

Because the right man won’t just want to date you.
He’ll already know he wants to choose you. 💍

You don’t need another situationship.
You need a strategy — and I can help.
💍 Join Last Year Single and let’s write your love story together.

ABOUT JACKIE DORMAN

Jackie Dorman is a relationship coach, matchmaker, bestselling author, and speaker who has helped over 1,600 people get married in just the last four years through her singles program Last Year Single and her proprietary HeartWork process. She calls Austin, Texas home with her husband of 18 years, David. Together they have a beautiful blended family with three adult children and two grandbabies.

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