She's been interested in him for three years now. We got together last May and we've been hiding it since. He told me it's time to tell her. She will not react well. I didn't want to date him at first for her sake, but I think he's the one. He actually asked me out New Years Eve but I said no for her. She's been hitting on him lately and leaving messages on his Facebook and texting him. It was his birthday yesterday and she left a "I love you Happy Birthday" type of message. So he told me today that enough was enough. If I don't tell her, he will.
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First I want to address a couple of things. 1. You did not make fun of 30schicky. 2. I don't see anything wrong with you dating this guy. The only thing I think you did wrong was keeping it from her. If you're put in this situation again, next time it would be wise to just tell her from the start that he isn't interested in her. He likes you... you like him... Sure, she likes him, but he doesn't like her. So, I would say the best way to break it to her would be first to tell her that he's not interested in her. That he just flat out doesn't like her. This would be easier than to straight up telling her that you're dating him. You can get to that at a later date. There's really no easy way of telling her without hurting her feelings. So, be ready for her to go ballistic. Most of the pain she would feel will be the fact that he does not like her. She will take it out on you, but the pain and anger she shows you will mainly be from the fact that he just isn't interested in her. If she doesn't believe you that he doesn't like her... you can tell her that he told you himself. Maybe even have him leave you a message saying that he doesn't like her. (leaving out the part of you guys dating) This way, you can show her the message that he doesn't like her... Then once she starts to get over the pain of him not liking her and she's over it... then you can tell her that you started dating him.0