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Dating Q & A – Are You A Transition Date Or a Keeper?


I started calling myself “Transition Man” because I’m usually the first guy to date a great women after she was dumped by her husband (often for a much younger woman). I prefer women my age, who’ve been through stuff and come out smarter and stronger. They know what they like sexually. And they like a guy like me, who aims to please.

I know how to soothe a woman’s bruised ego after a big break up, and get her to see the best in herself again. That’s when she breaks up with me to date other guys. She’s not ready to settle down so fast after her long marriage broke up. Okay. I get that. I had a ten year marriage.

I want to win the heart of a wonderful women and have a relationship that lasts. I’d like to be a keeper instead of a transition man in a rebound relationship. Any suggestions?


A comedian once observed that unless you’re the first and only, you’re always in a rebound relationship. So you’re not the only single adult with this dating challenge.

I like your definition of a “transition man”, who soothes emotional bruises and brings out the best in your date. Yet there’s a reason you feel unsatisfied in this role. A healthy relationship works both ways.

Emotional support needs to be mutual, freely given and received by each dating partner — if you want to make the transition from a casual to committed relationship.

A newly-single woman may not be emotionally available to consider your needs so soon after her break up. Don’t take it personally, since it’s really not about you. Why?

The first year after your big break up is the ideal time to discover the person you want to become in your new single life. The new you will want new things in a new relationship.

You discover the new you by asking yourself new questions:

What love lessons can you learn from lost love in your recent relationship?
What emotional baggage can you pack up and leave behind?
How do you help you (and your children) thrive?
What dreams can you revive?
What passions can you pursue?

Typically the passion of a new romance can distract men and women from the personal growth that can occur after the death of their relationship. Since you’ve gone through a series of break ups with great women, you’re ripe for some personal growth. Change is the catalyst for growth.

Are you ready to change your dating pattern?

Since you’re no longer satisfied with short-term dating relationships with newly-single women, you can change your dating criteria. You can choose to date women who are emotionally ready for a relationship.

How do you find out if someone’s ready for a relationship?

By asking questions during a first or second date or during email or video chats on a dating site before you decide to meet in person.

What if you meet a fabulous, freshly-single woman who hasn’t had a rebound relationship? What if she hasn’t worked through the emotional blocks that stop her from loving again?

You can give her your card and ask her to call you in a year. Tell her she’ll be ready for a fabulous relationship with you after her year of personal growth that follows a break up.

She’ll be intrigued by your confidence and wisdom, and you just might hear from her again. But don’t wait around. Carry on with your search. You’re one step closer to meeting your love match who’s emotionally ready to build a great relationship with you.

And I invite you to meet positive, successful singles in our holistic dating and travel site. No more blind dates, since you meet in video chats, live events, or dream travel at dream prices. Meet awesome singles now. Click SINGLES CLUB in the menu bar and sign up.

Love deeply and live your dreams now,

Hadley Finch

About Hadley Finch

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