Asking out a guy whom you have had the longest crush on, isn't a peace of cake! But it isn't just the asking out part that is difficult , there are a lot of don'ts that you have to keep in mind and make a mental note on! Once you follow these pointers, its love love all the way....
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#1 Don't Hit On Him When He's Got A Girlfriend
This one could work out well for you... but do you want it to? It'll also tell you a lot about him. Either he's not interested, or he's willing to cheat on whoever his current girlfriend is. Eventually, that might be you.
#2 Don't Have A Friend Do It For You. This is a technique that belongs in middle school. At best, even if he's saying yes, it puts him in an awkward place. It feels decidedly immature.
#3 Don't Play Hard To Get
This doesn't necessarily "count" as asking out, but it seems like enough people think it's a great way of putting yourself out there. It isn't. It just makes you look like you don't like him. To be fair, there's a difference between teasing him a bit and just ignoring him and making it seem like there's no hope. Those differences should be obvious. If they're not obvious, then never do this.
#4 Don't Ask Him Out And Then Cancel Or Reschedule
This is a great tip for anyone making plans, but I think it goes doubly so when it's for someone you're really into: don't make plans you're not sure you can keep.
#5 Don't Ask Him Out And Then Take Him To A Party
This is not a date. It might be fun for both of you, but it likely isn't a great way to get to know each other, especially if he knows no one and isn't exactly outgoing. Try and keep to something more one-on-one for the first date.
#6 Don't Pretend Just To Impress Him
Don't ask him out snowboarding if you've never gone before. You will die. Just do dinner or something. Or, tell him you always wanted to go and ask him if he wants to try too. Just don't pretend to be someone you aren't.
#7 Don't Ask Him Out When Your Are Too Busy
Leaving early is almost as bad as canceling, and it makes it seem like you don't really care about the date. It's a real confusing set of mixed signals.
#8 Don't Ask Any Of Your Friends To tag Along
This will just make it more awkward. A double date is fine, but asking your friend to come along and be the third wheel just because you're anxious is a bad idea.
#9 Don't Overthink It
This is it. You might not have a lot of experience taking the initiative, but don't worry. Just be yourself, the magic was inside you all along, etc. If he's going to say "yes" it doesn't really matter what you do anyway. And he's going to say yes. Because I believe in you. But more importantly, you believe in yourself and junk.