Unrequited love on a long vacation

Dear Meredith,

I am in love with one of my best friends and I've hidden my true feelings for a very long time. Staying "just friends" meant I often got more of him than the many women who have come in and out of his life over the past decade. He tells me the current woman he sees is not his future and that he is not in love with her.

Now we are on an idyllic vacation for a few weeks, often sharing a hotel room. Lots of long, wonderful, talks. Our backgrounds are so similar it is almost eerie. Ditto for hopes and dreams. When he describes his perfect woman – intelligent, loves family, pursuing an artistic passion – he is describing me. I think perhaps he is vey scared; he knows his track record isn't the best. Many women have loved him, and he's broken a lot of hearts.

People say he can't commit, but I think it goes much deeper than that. I think he's very scared. The one time we crossed the line last year (we were on a different trip at the time) he was devastated, and his main comment when we talked about it was: "I don't want to lose you." I spent the day away and when I got back to the hotel room that night, he came to the door in his underwear and enveloped me in the tightest hug, repeatedly saying how sorry he was. And how much he loved me.

How do I deal with this? I love him so much.

– Just A Friend

You need to tell him how you feel. Not on this vacation – because there's no great place for space if you need it – but when you return. Please.

I know you're scared to lose him and that you don't want to ruin what you have, but it's already a mess. This unrequited longing has you writing a letter to an advice column while you're on vacation. I very much appreciate the letter, of course, but you should not be doing this on what's supposed to be a happy, platonic trip.

You should not tell him you're his perfect match because at this point, you can't be sure that's true. Just explain that you'd like to explore your romantic feelings for him. He'll say he's afraid to lose you, but you can let him know that things are going to have to change no matter what. You can't maintain this routine, so it must become something else – even if that means taking a step back.

If I had an advice time machine, by the way, I would go back to the early 2000s and tell myself this: When you pretend to be your unrequited love's best friend, you do not get more than the "many women who come in and out of his life." They get to date him or move on, and you don't. It's better to ask for what you want.

– Meredith

Readers? How should she deal with this? Should it happen on vacation?