How should I handle this ?

I think it's totally your decision of whether you are interested in getting into it or not. If you are not truly interested and are just feeling pressured by your mom or something or are just feeling a bit desperate or something, you have a right to say no if you want to. After all, it's your life, and if you're not sure that this is a situation that you want to get involved in, you have a right to choose what you want to do and not allow other people to put pressure on you. Also, you're the one who will have to be on the blind date with this dude if you decide to go for it, not your mom or anyone else, so you have to decide whether you want to or not. If you don't want to, I say, "Just say no!" Well, good luck! :)

That's up to you. Do you want to pursue it? Only you can answer this.

As far as the email goes, it's possible he has email settings that restrict certain kinds of email, but since email technology eliminates email in broad strokes, rather than in specific detail, he can't receive yours for some reason. Also, guys are not always very tech-savvy, so he may not be aware and/or doesn't know how to fix it.

But even after that, it comes down to whether you think it's something you want to do. I'll give him one thing, he's employed.

I say give it a shot. If it doesn't work out at least you tried:) Who knows he could be the love of your life:-D