How do I keep things casual?

What relationship stuff is stressing you out? Send it to [email protected] or fill out this form.

More updates, please: Former letter writers ... where are you now? Did our advice help? Send us an update to [email protected] with “update” in the subject line. Make sure to say which letter you wrote. Let us know what happened.

Dear Meredith,

I'm 55, divorced for the better part of a decade after a long marriage. While I've dated over the years, I've not found a steady relationship or gotten serious with anyone. I enjoy the freedom that living single provides, and am not looking to get married again, but I was hoping to find someone to care about who also cares about me.

A year ago, I met someone and we casually dated for about five months. We went away together for a weekend, but right after we returned from the trip, he ghosted me. Even though we were only casual, I was deeply hurt by the rejection and briefly went back to therapy to process a lot of emotions it brought up about past abandonment.

He eventually reached out to apologize for his behavior and offer an explanation, and ultimately we decided to keep our distance and just be friends. However, over time, we wound up rekindling the romantic side of things and started dating again, but agreed to keep things casual. Fast forward to today – I now find myself having deeper feelings for him. I care about him very much, and miss him when we're not together, but I don't believe he sees me the same way. I love spending time with him and we have a blast together, but I fear that each time I see him will be the last time, and he will reject me again. In the days after we see each other, I get sad because I'm wishing that he returned my feelings and wanted a relationship, but recognize it's probably never going to happen.

I feel like I need to take some kind of proactive steps, but my friends are advising to ride it out and just keep him around and have fun with it while it lasts. (I'm not getting any younger, I've been single for a long time, and they know how alone that I've been.) I could use an opinion from someone with an objective perspective. Any advice?

– Casual?

I wonder if your friends understand that staying with this man is making you lonelier than you might be if you were 100 percent single. If he wasn't around, you'd miss him, but you wouldn't have to deal with the sadness that hits you after he's gone. It sounds like your brain is telling you, "You can't handle being casual with this man anymore! It is bad for you!" … but you haven't taken steps to deal with the problem.

I disagree with your friends, even though they probably mean very well. You’re not getting any younger, so why would you stay in a situation that leaves you feeling empty? Tell this man you're looking for more – that you no longer feel casual about him and want to be a couple.

You can explain what that would mean to you – how it would look and what you desire. If he's not enthusiastic about trying, you can break it off. Take space and be sad, and then, soon enough, you'll remember that everything works without him too.

He's not the only man out there, and at 55, there are probably a lot of people who seek what you describe in you first paragraph. It might be nice to be able to look for them.

I'm all for being proactive, even if it means letting go.

- Meredith

Readers? Ride it out? Enjoy and have fun? Or ask for something more than casual? Or just break if off now?