Dear Clueless,

So there's a boy who likes you and you don't know how to let him down gently? Since your question is fairly general and I don't know the specifics of your situation I am going to answer your question with two different scenarios that I have been through.

How to go about rejecting him nicely depends on what your relationship with him is like to begin with. Are you friends and he wants more?

Scenario number 1: A Good Friend Wants More

My best friend (we'll call him Nick) of three years and I met when I was 15 and he was 17. He had just moved to my city and our moms knew each other. Of course, as any mom does, my mom insisted that I call Nick and be his friend since he didn't know anyone here.

My first thought was 'hmmm, a 17 year old boy...could be good...." Well, Nick turned out to be the nicest, sweetest, kindest possible guy I could ever have met and we began hanging out all the time and I would tell him about my guy stories and he wouldn't really listen and pretty soon I realized that he liked me more than just as his friend.

There were two ways that I could deal with this:

1. talk to him openly and tell him I just wanted to be friends
2. just not hang out with him as much and be less friendly.

I chose the second option and I basically gave him the cold shoulder. He had no idea what to do because not only did he like me as more than a friend, now I wouldn't even hang out.

To make a long story short he asked me to his prom and I went with him but that same night he tried to kiss me and this time I chose option number 1. I came right out and explained that while I liked him a lot, I wasn't interested in being more than friend. I was lucky because Nick understood and subsequently he has become one of the best friends I could ever have imagined having.

The moral of that scenario? If in fact this guy that likes you is a good friend, or someone you would like to keep as a part of your life, I would highly recommend making the effort to talk to him and simply explain that his friendship means a lot to you, but that you aren't interested in having anything more with him at this point in time, or maybe ever. Who knows? Maybe down the line things could be great for you two.

Scenario number 2: A Stranger Asks You Out

Is he some guy you barely know; maybe from school or work? Chances are good that maybe this guy is just some guy in your math class that sits way in the corner and stares at you all day. Or, maybe he's a guy from work who you have never said more than two words to.

I have a great stoy about what can happen if you are NOT honest.

Whatever the case is, if he is a guy that you barely know then basically you don't have to worry about what to do until he gets the guts to strike up a conversation with you. If this has already happened, then I would suggest, as in scenario #1, that you are honest with him about what you think.

In this case since he doesn't know a lot about you, it is easier to be more general. Maybe something like "I'm just not interested in a relationship right now" or even, "I have my eye on someone else right now." Sometimes this can seem harsh but I think anything is better than leading him on and then hurting him even more once he's grown to like you more than he did to begin with.

The other side of this scenario is the potential for him to be someone that you could really grow to care a lot about.

My ex boyfriend was a guy that I met at work. We will call him Jack. Jack was a waiter and I was the new hostess and as is the situation in our restaurant, the new hostess is always the object of everyone's affection until someone snags her or a new girl arrives on the scene.

Well, for the first three months that I worked at this restaurant, Jack pursued me. Time and time again I avoided hanging out and made excuses not to give him my number. It wasn't that he was unattractive (he was gorgeous) but I was a bit weary of dating someone I worked with AND I wasn't sure if he was my type as far as personality went.

Finally one night I told him to bring some friends and come hang out with me and my friends and so he did. We had the most fun I had had in a long time but I was still unsure. Somehow Jack got my number and called me a few days later and we talked for three hours on the phone. Instantly I realized that maybe this guy was for me. He ended up leaving our restaurant which was even more convenient and Jack and I dated for a little less than a year.

He turned out to be the most amazing boyfriend I could have hoped for and he treated me like a princess. My point is that you shouldn't dismiss this guy as someone you aren't interested in until you get to know him better.

So, how do you let this guy down without seeming insensitive, especially since he is so vulnerable? Do it very gently. The only advice that I can possibly give you is to be careful how you say it to him but don't spare his feelings.

I agree. I once had to break up with a guy twice, because I used too much sugar coating the first time.

Tell him how it is without sugar coating it because if you aren't completely honest and open he may not get the message.

You need to tell him that you are not interested in a relationship right now for whatever reason it is that you feel the need to reject him and make sure that he understands what you are saying. Don't lead him to believe that there may be hope for the future if there is none. The only way to ensure no future problems will occur is to be 100% honest with him.

Just like girls, guys don't want their feelings played with and they want you to tell it to them like it is, even if they are vulnerable. He needs to hear it from you, no one else, and he needs to hear it soon.

The longer you leave it the harder it will become for both of you to deal with it.