I’m in a relationship with long-term promise but i’m not feeling loved. When do I move on?

Dear Wanda and Wayne,

“Jason” is in his 50s; I knew him casually and for about two years, he offered me his number and asked me out, so I knew he was at best, patient and persistent. He said he was looking for a relationship that would last. I finally gave in and agreed to a first date.

We have now been dating for 10 months. He is kind, clear, states intention, protective, consistent, unfailingly honest and fun.

I have fallen in love with him and have told him twice how I feel. His reply each time was, “Thank you.”

Jason says he “likes me a lot” but doesn’t love me “yet.” He has talked about being devastated when his last relationship (with a much younger woman) ended after 10 years. They broke up two years ago.

Before we started dating, I had come out of a long relationship that lacked serious commitment. I spent 18 months single before my first date with Jason. I had a lot of time to reflect and I vowed to myself to only date people who wanted to find long-term love.

I do feel like Jason and I are on a good track. We’ve spoken of a shared future. I’ve made it clear I wouldn’t live with him unless he loved me, which surprised him.


How long do I wait for him to love me? I’m 59 now and don’t want to have another long relationship with someone whose feelings won’t progress into love. It’s so difficult to know when to leave if I’m not loved. It’s starting to affect my self-esteem as I’m imagining I don’t measure up to his ex (and therein lies madness).

Thank you.

Wanda says:

In your letter, you pose many issues and questions of timing — whether that’s time between relationships, duration of existing or past relationships, and the final and very important question: how long one should remain in a relationship that isn’t delivering what they’re seeking before moving on?

Let’s start at the beginning of your story. Jason’s last relationship ended two years ago. He also started pursuing you … two years ago. While you didn’t say yes right away, he was focusing on you (and perhaps other women as well) instead of working to heal and learn about himself after a bad breakup. Jason went straight from monogamy to rebounding and now, presumably, to monogamy again. It’s possible Jason never took the timeout he needed to be ready for vulnerability and love.

How long should you wait to see if he can get there? Everyone will answer this differently. Some might bail the first time a confession of love was matched with a “thank you.” Others might hang on hopefully for years. There are many approaches you could take. Consider giving yourself an exit date if he hasn’t risen to level L Word. You could also tell him you have a deadline — which is pretty much an ultimatum, and clearly establishes expectations and puts issues out in the open.

Bottom line, you can’t control Jason’s emotions. You can control your own timeline and behaviors. So focus on what’s within your power and be honest with yourself.

Wayne says:

Forget about Jason and go back to the promise you made to yourself. You survived a long relationship, spent more than a year working on yourself, got your feet solidly back on the ground, and found clarity in what you wanted moving forward from a relationship: you were only dating people interested in long-term love.

And here you are now, a year into a relationship that seemingly has long-term promise, but also includes a partner who for whatever reason can’t or won’t express, or possibly doesn’t even feel, a mutual love for you. Ten months of communication and connection, intimacy and intention, yet you’re feeling sad and confused, and he’s still unsure if he loves you? Red flags galore!

And let’s be real: you’re nearly 60. How many more years, months or even weeks do you want to burn with someone who can’t even say he loves you? Look, it sounds like he’s a great guy and he treats you well, and you two clearly have something cool going on. And for some folks, that’s more than enough.

But you want more. You promised yourself more. You deserve more. So don’t tell us any more — tell Jason. As Wanda said, it’s time for you to let him know that if he can’t sort out his feelings for you as you approach a year together, you’re clearly not on the same page about love and the future, and that you’ll be moving on not moving in. Hopefully, he’s just scared, gets over it, tells you he loves you, and you both enter a long-term relationship powered by love. Or maybe he’s just not there and never will be. Either way, stick to your guns and the promise to yourself. Good luck!

Wayne and Wanda

Wanda is a wise person who has loved, lost and been to therapy. Wayne is a wise guy who has no use for therapy. Send them your questions and thoughts at