Since You Asked: Should I Confess My Unrequited Love?

When I was 19, I met Nick*, who was 24 at the time, and the lead singer of a very well known indie Northeast band.  We became friends, and since I lived in a different state, we emailed back and forth, talking mostly about bands we liked, and sometimes I'd send him things that I'd written (mainly short stories) because we connected so well on the writing level.

Later that year, the band went through a very nasty break up and he found himself heartbroken but also excited about the possibilities of being a solo artist. I supported him from the very beginning and for the first time, I felt like I belonged somewhere, like I fit in, and I was accepted for who I was in his music scene.  

I also developed some pretty serious feelings for him in that first year of knowing him, but I always kept it to myself, out of possible embarrassment, and also because he had a girlfriend. But our friendship continued to develop and I started to take on a larger role in helping with his music career - promoting, listening to demos, previewing albums before they were cut, etc.  

A year after I graduated college, I moved to the same state that he was living in, for many reasons, music being a big part of my decision.  The move only brought us closer as friends and I eventually took over managing certain aspects of his career.  

Perhaps I should also mention that he's a serial monogamist who can't be alone, and he's been in 3 serious relationships in the years I've known him.  I've had my own relationships, too, but I've always loved Nick.  He broke up with his last girlfriend in the fall and since then we are more open with each other than ever, physically and emotionally. We've always been huggy with each other, but since the fall its escalated to his arm around my waist, like not in a friendly way, this hand holding business the other night, and generally finding reasons to touch each other.

I've been in love with him for years, but for the most part I've pushed it away because he's so tied into the social scene and music scene where most of my friends are, where I feel most like myself.  I would be devastated to lose that, and to lose him, if things were to go badly.  I am basically at a loss of what to do - he has initiated so many intense moments, but nothing ever comes of it.

I know if I told him how I felt and he said he didn't feel the same way he'd be very gracious and caring about it, but the thought terrifies me to no end. I need some sort of plan, idea, scenario, where those words don't have to come out of my mouth because I'd probably pass out.  Help! 

--Unrequited Lover 

This sounds to me like it came straight out of a movie script. But this isn’t the movies--it’s your life--and you can’t just waltz up to this guy and blurt out, “I LOVE YOU!” because you would be risking far too much by doing it that way. It’d probably scare the heck out of him, too.

It sounds like you guys have definite chemistry, and other people likely pick up on the sparks between you. You already have a great foundation built over many years of friendship. But you are also entangled business-wise and you said it yourself that this guy is a serial monogamist... so I would be wary in entering into a relationship with him because you know his relationship patterns.

Let me bring you down just a little more before I build you back up.... Musicians can be fickle, could be that he just likes the chase? Are you sure that these moments he is creating that seem so intense between the two of you aren’t some dramatic ploy he likes to play at? Does he enjoy that you are one of the only women he knows that he hasn’t dated and he likes to keep it that way?

My sister in law has this great sticker on her water bottle, and it pretty much sums up your dilemma:

You have a decision to make and your problem is that you just don’t want to put your feelings on the line. That’s understandable... but to let him know you are interested in him, you don’t have to put all your feelings on the line. Like I said, you don’t want to scream your unrequited love from the rooftops. What you want to do is play it cool.

You sound like the kind of gal who likes when a fella makes the first move, and that’s cool, but are you in a prime position to have him make that move? When you are alone with him have you ever dropped a bigger hint, for instance saying something like, “If you wanted to ask me to dinner, or on a date, I might say yes”? Maybe it seems obvious, but it’s a good way to see if his physical displays are more than just “friendly” gestures.

You could also be sweet about it and say something like, “Of all these women you have dated over the years we’ve known each other, did you ever think of me that way?” It’s a direct question that he could easily wiggle his way of if he didn’t feel the same. Or there’s always the classic, “Hey you know, we’re both single these days...isn’t that funny?”

The biggest thing you need is just some self confidence, and if you ain’t got it, then fake it til’ you make it. Play it cool when bringing it up and don’t let him know exactly how much you do like him. That way, if he doesn’t return your feelings, your friendship can be maintained because he won’t feel it’s awkward... in the end, though, if this guy doesn’t return your feelings, then you need to move on. Take a day to listen to sad music over a tub of ice cream and then forget about it!

There are tons of great guys out there and life is too short for unrequited love stories. Love is to be shared! So get your piece off your chest (in subtle way if you need to) and see what happens. If this guy can’t pick up what you’re throwing down, throw it down for someone who wants to pick it up!

And as far as alienating yourself from his music scene? Keep in mind, one person does not a scene make! What you are a part of is bigger than him--you’ve already made the connection with the people around you--you should be confident about your place in your circle of friends.

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