Finally, we’re both single. Now what?

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Hi Meredith,

I have a situation that's been at the forefront of my mind for the last eight years, give or take. We met in college and hit it off as friends. We've both been in and out of relationships throughout those eight years, and have even had the "Are you friend-zoning me or is there a chance here?" conversation two years ago. At that time, I was in a relationship, so I probably shouldn't have been having that talk with my friend, but it happened anyway and I got my answer: "No, I thought YOU were friend-zoning ME so I just never tried anything." A wave of relief, but also total confusion came from that conversation because again, I was still dating someone, and my friend seemed to take a step back after that. He took a few weeks of space but then we went right back to our usual hangouts and flirting here and there.

Fast forward to this past fall when I finally ended things with my boyfriend, and my friend got out of his relationship not long after. This is the first time since college that we've both been single at the same time and I'm afraid I'm getting my hopes up for something that will never become anything at all. All of my friends, and even my family, have always said that it will happen eventually and that I just need to be patient. More recently, he's started to invite me over for dinner once a week and I've been loving it. He puts serious thought into the meals he's making, preps and cooks everything, and we spend the night enjoying each other’s company. I guess my question to you is: Do friends typically do things like that or could this maybe be his way of slowly figuring out if this is something he actually wants?

I know the easiest way to figure all of this out would be to just ask him, but I've been the person to bring up my feelings twice already and feel like a broken record at this point. I've been vulnerable with him and a part of me wishes he'd do the same with me for once. I don't want to drive him away because I genuinely value our friendship more than most in my life, but I also don't want to have to watch him date yet another girl I know isn't right for him when I'm standing right in front of him. When do you decide it's worth the risk to tell someone you still have feelings after all these years – or when it's not, and you should finally move on from it in a romantic sense all together?

- Slow Burn

"I know the easiest way to figure all of this out would be to just ask him, but I've been the person to bring up my feelings twice already and feel like a broken record at this point."

Technically that's true. But let's remember that the last time you brought up your feelings, he told you he reciprocated ... and then you continued to date your boyfriend for another two years. This friend was brave and forthcoming with his feelings, and the result was ... nothing.

You might feel like you've done all of the emotional heavy lifting in this relationship, but really, keeping your feelings to yourself is a lot more work than telling him how you feel. Also, maybe these dinners are a big emotional lift for him. He's inviting you. It sounds like he's initiated all of your recent plans.

Just so you know, I don’t think you need to have some monumental talk with him about what happens next. All you might want to say is, "Finally, we’re both single. What if we kissed after dinner and see how we feel?" Slow burns can put a lot of pressure on people, especially when friendship is on the line. It might help both of you to hear that you don’t have to start a new chapter of your relationship with all the answers.

It's a pandemic, and I'm not sure where you live, but the social constraints on our lives have left us no room for mind games. If you want to stay close to this person and consider experiencing the romance you’ve always wanted, take that first step and tell him how you feel. Yes, it's worth the risk. If he doesn't want what you want, you can take your space.

– Meredith

Readers? Should the LW bring up feelings? Why hasn't anything happened yet?