Nice Guys Finish Last

The comment:

What do you do if a really nice guy confesses his love for you, but you just don’t feel the same way? How do you let him down easy? I know honesty is the best policy but I don’t want to hurt his feelings because he is such a nice guy, and deserves a great girl. I just don’t want to lead him on.

This is the worst. I mean, seriously… the worst.
In this situation, you’re usually stuck in a place where nothing you say feels like a good enough reason to not reciprocate the interest. They’re nice. Like…incredibly nice.

My aunt once pulled me aside after I introduced her to a nice guy who had expressed interest in me and whispered in my ear, ‘The nice ones don’t come along very often… don’t let him go.’

I might have panicked a little. Should I date him because he’s nice? Is she right? Am I going to let this nice guy go and then not meet another one for ten more years? I began asking myself what matters most in terms of character. The more I thought about it…the more I thought about what it would be like to be partnered with a man through life as I have kids, as I get sick, as I am moody, as I am crazy… and the more I realized that ‘nice’ should be pretty high up there on the list. Genuinely nice… not just fake nice.

But as time wore on, I just knew I couldn’t do it. Nice wasn’t a good enough characteristic to make up for things that were lacking. Nice didn’t mean that I could forgo all the other things that I cared about. Nice didn’t generate attraction. I didn’t really feel like convincing myself to date someone was really the best way to enter into a relationship.

So here’s the tricky part, the question that you asked… how do you let the really nice guy down easy?

Shoot.
It’s the worst.
Honesty is the best policy. And so, I think you have to be willing to tell him exactly what you told me. On some level, any time you tell a guy you’re not into him, it’s just going to be hard and awkward and uncomfortable. Unfortunately, telling the nice guy that you’re not into him is even harder because he’s only been kind to you.

Here are some thoughts to make the unbearable a little more bearable:

• Nice guys deserve the truth…especially if they’ve only been kind to you. The nice thing for you to do is to be honest with him and upfront with him. I’m not saying that you need to tell him every detail of why you’re not interested in him, but if you know you’re not interested in him…. you need to tell him as soon as you can. No delaying. Be kind to him through not leading him on any more than you probably already have. Make sure you don’t leave room for there to be any alternative… (i.e. don’t say things like, ‘I just don’t think it’s going to work out right now…‘ the right now leaves room for future possibilities). 
• Encourage him. If you appreciated the way that he pursued you and showed interest in you, be sure to let him know. Make sure he knows that you really do think he’s incredible and that you felt really honored in the way that he went about asking you out. Be sure to let him know of the specific ways that were especially great so he can at least take those things on with him when he meets other great girls that he’s interested in. He may feel, in the rejection, that his approach was all wrong, so you definitely need to encourage him to keep doing what he was doing… you’re just not the right one to be the recipient of his affections. 
• Give him space. Since he’s a nice guy, you probably enjoy being his friend. So, as cliche as it sounds, I think it’s okay to give him room to continue to be your friend if he wants to. But, also be respectful that he may not want to and maintaining a friendship with him may be harder for him than it is beneficial to him. Be willing to talk about this with him if he’s up for it.  
• Don’t initiate. In giving him space and offering your friendship on his terms, you’ll need to back off. Let him communicate with you when he wants to and when he’s ready to. He may need time…he may never even want to. Be kind when you see him and when you hear from him, but let him approach you. At least for a while. You mostly just want to avoid doing/saying anything that could send him the opposite message of ‘I’m not interested…’. 
• Don’t tell all your friends. If there’s anything worse for a guy than rejection, it’s being rejected when everyone else knows about it. There’s no need to ask all of your friends for advice if you know you’re not interested. Help keep his pride in tact by not spreading rumors or talking about the situation.