Was discussing this with a friend of mine; what's the best (least painful) way to let someone down, when you're not interested in them physically/romantically?

Quite honestly, as upfront, frank as you can be – yet genuine and sincere. If they want to talk about how they feel, let them, and discuss it with them.

Though we might want to get it out of the way as fast as possible and move on with life (as with all uncomfortable situations), we mustn’t forget that this person may be dying inside, sheltering this idea of you; letting it fester and grow. They may love the idea of you more than you know.

Speak calmly, understand and take appreciation in what they say and respond back. Laugh and joke if tone permits; if all goes well, you might be giggling about it by the end of the conversation.

Best advice I can give – stuff like this is never easy.

Just be completly honest…Tell them in the nicest way possible that they’re a great person but you think it would be better if you were just friends. Depending on the person they may not wanna be friends afterwards if you tell them the wrong way. Just be honest but dont mean.

Maybe the sandwich method.

1. Thank them/I’m flattered
2. Compliment them (you’re a great guy blah blah)
3. Decline (it’s not the right time whatever)
4. Give them best wishes/good luck (you’re a great catch for any girl blah blah whatever)

Do it kind of fast like a sales pitch so that they don’t realize you’ve dumped them until your spiel is over and their smiling on the way out the door.

Lie about your motivation for not wanting a romantic relationship – people don’t really get over being told that they’re not attractive. Like, I’d say something like “I’m just not interested in seeing anyone right now, plus I don’t want to make our friendship weird. You mean too much to me to risk muddying up our relationship with romance.” Friend in question should get the picture without you having to come out and say directly that you don’t want to be with him/her.

Very diplomatically, something like “Oh, jeez. You’re an amazing person and a great friend but I’m really not looking to get into a relationship”

@Grisaille: I can’t top what you’ve just written. No one wants to be complimented with “you’re great… but” and most would appreciate the being heard out.

Do not assume you always can salvage a friendship. Your first priority should be to be clear with them, and second to see if a friendship is possible for them.

I would say be direct, but not hurtful. So, something like, “I like you very much as a friend, but I’m afraid there is just no chemistry for me.” (So, nothing wrong with them, just not right for you.)

@wildpotato Lying does not seem like a good idea to me, especially if you want to stay friends. What if you say you are not interested in a relationship and them Mr./Ms. perfect comes into you life the next week?

Least painful can go two ways. Intense but over quickly, or less intense but drawn out.

I feel that being blunt is the best approach – having tried the other approaches and found them ineffective.

Many people make an attempt to stay “friends” and don’t want to anger the person that they are dropping – try to do it “nicely”. Life doesn’t work that way. Sooner or later they will feel anger toward you.

I probably wouldnt start with the ” we need to talk” because they would figure it out right away i would tell them exactly what your feeling whats bothering you, and if you just know you cant fix it break it to her\him gently the way you would