I’m wondering if he’s ready for more

Hi Meredith,

Last summer I started a friends-with-benefits relationship with a man I met on Bumble. We had great communication and defined the terms – that we would be friends, get physical, and go out every once in a while. We had a good routine of hanging out at my place, watching shows, talking, and hooking up. One night I invited him for dinner/drinks and he resisted (we hadn't done anything outside my place yet). He was worried I wanted more, even though I was always very clear about what I wanted from our casual relationship. Turns out he was just in a bad place with his mental health and needed to focus on himself, which he did. We cut ties and didn't talk for several months.

He reached out four months ago because he really needed someone to talk to and knew I'd be a good friend. We eventually got back into our old routine. Here’s the thing – over the past few months we've been closer than ever, finding out we have so much in common, and doing a lot of activities like movies, breweries, home improvement projects, and lunches. He even wanted to meet my friends and come to my birthday dinner. He's so sweet, my biggest cheerleader, and we can talk about everything. And the physical chemistry is great. You must know where I'm going with this. I'm starting to wonder if he wants more. We talk every day and are much closer than ever. I've never considered him someone I'd date only because he's never wanted a real relationship, but if he did, he'd be my perfect guy. I'm afraid to lose this close friend by asking for more, but I'd like to try dating for real. I think part of me is also afraid someone could like me enough to have "benefits" with me, but not enough to date me. How do I approach this?

– Benefits

You say you want to try dating for real, but it sounds like that's already happening. You're going to breweries and movies together. You seek each other out for emotional and physical intimacy. The only thing that's missing is an acknowledgment that things have changed. That's what you need to talk to him about.

Tell him you're enjoying all the ways this relationship has evolved, but you're wondering if he’s noticed, and what it means to him. Talk about what's working and what would make you more comfortable with your arrangement. Revisit those terms and adjust.

If he says this is temporary – that he's still opposed to allowing this to grow – you'll need to make choices about how much time you spend with this man. You call him a close friend, but your feelings for him are not platonic. I mean, he's apparently your perfect guy. Your romantic connection is the most important thing. Please know that if he rejects you, it's not about him wanting "benefits" but not wanting to date you – because again, he is dating you. This is about whether he's willing to plan with someone, and to be accountable to a partner. He might not be ready.

You're afraid that if you ask for more, you'll get less. That makes sense. But you've hit the point where you need information. It's time to get it.

– Meredith

Readers? Time to ask for more? How should the LW frame this?