‘Too old to do a non-relationship’

Dear Meredith,

I have been friends with "Joe" for about eight years. We started hooking up about two years ago, a few months after I broke up with my boyfriend (a friend of his). From the beginning, he was pretty clear that this was just for fun and that he wasn't looking for a relationship. I was OK with that given I had just broken up with my boyfriend of many years and was about to start graduate school. I also went on a few Tinder dates around this time, which he supported.

Cut to two years later and we are talking every day and hooking up when he's in town every few months. About a week ago, I decided I wanted to start dating again to maybe find something a little more serious, so I re-downloaded Tinder. In the spirit of honesty, I told Joe about it. He seemed supportive – until I texted and said that I kind of liked a guy I'd gone out with. Joe got silent and weird after that for a few days, and then his tone with me changed (it became more platonic). It made me miss how things were, even though we aren't even in a relationship.

My question is not if I should have a conversation with Joe, because I know I have to say something. I'm wondering how I should start the conversation and what I should say. I really, genuinely like Joe and his company, and we click in a way I haven't with others, but I'm getting too old to do a non-relationship. I fear I'm sticking around for an easy confidence boost instead of taking chances in the scary world of dating. Any help is appreciated!

– Confused in Boston

You know exactly what to say. You said it all in your letter, right?

The script would go something like, "Joe, I'm conflicted about this Tinder thing because what we have is great in it own way. Do you think we're making a mistake by not taking it more seriously? I went on Tinder because I'm getting too old to do a non-relationship, but after two years, I've lost track of what we might want from each other."

Maybe Joe will tell you he wants more than a casual relationship. It's also possible he'll say he prefers the status quo. If that's the case, you'll have to get used to his new, platonic tone. You might even have to take a break from those daily conversations.

It would be difficult to minimize Joe's place in your life – to live with less attention – but you don't want him distracting you from finding what you really desire. If he wants to keep it casual, you must set new boundaries so that you dive into that scary world of dating 100 percent single.

– Meredith

Readers? What should she tell Joe?