Dealing with unrequited love

Dear Meredith,

I have started to write this letter to you so many times and stopped -- maybe because I'm afraid of what your answer could be.

I'm completely in love with one of my best friends. Hopelessly, stupidly, Rachel McAdams movie-type love. I've known him for over a decade and the more I know him, the more I fall for him over and over again. And inevitably, there are multiple complications. Like the fact that he has a girlfriend of several years. And I can't tell you this story without the full disclosure that I'm almost 30 and I've never had a boyfriend. I've casually dated, and I've just never found someone that measures up or gives me the feeling that he does.

I've done so much to get over him, and to put myself out there for other people. I've agreed to set-ups, tried online dating, and even tried to slowly back off from our friendship. I spend a lot of time wishing that I could find someone else who makes me feel the way he does, because it doesn't seem fair that I'm so stuck on someone so unavailable. I truly don't think that the lack of availability is what appeals to me. I'd marry him tomorrow if he asked.

Even though I'm sure he will end up with the girl he's with now, I still have a small flame of hope that he feels something with me. I feel as though our chemistry is electric and I know he can feel it too ... even if it's too much for him to even consider going down that road. We've done a lot of growing up together and it's overwhelming to think about. Sidenote: I'm also pretty plain-looking compared to the others on his dating resume.

So, any chance you think he could have been harboring secret romantic feelings for me over the past years? I know I watch too many rom-coms, but I figured this letter was worth a shot. Thanks in advance for any advice.

– Wish I Could Make Him Really See Me, Nashua

Trust me, he sees you. And maybe he's had some feelings here and there.

But ... if this were a Rachel McAdams movie (romantic comedy, not Sherlock Holmes or Woody Allen), she wouldn't wind up with this guy, right? She'd wind up with some new person at the end of the film. I mean, that's how this works. The ideal narrative isn't that he falls for you; it's that you realize that you've been pining for someone who hasn't earned it. He's been content to be with someone else for years. That's not OK.

I believe that he's fantastic, but the fact that you say that you'd "marry him tomorrow" means that you've lost perspective. You don't know what it's like to be bored of him. You don't know what it's like to count on him as a romantic partner during a tragedy. He's become something imaginary in your head, and you must believe me when I tell you that there’s no way he'd measure up to your fantasies.
You need to keep dating and widen your circle a bit. And you probably need to minimize your interaction with him and make plans with new faces. I know that you know all of this, but you have to start believing it. Trust me when I tell you that reality with someone new will trump this fantasy relationship.

Readers? Is there any chance that he has feelings for her? Should she tell him how she feels? How can she get excited about dating other people? What's happening here? Help.

– Meredith