Start up a conversation with someone you like. If there is somebody you have your eye on, talk to them about anything and try to gradually change the topic to Valentine’s Day. If this is hard to do, on the week of Valentine’s Day, casually go up to them and ask if they’re doing anything interesting this week, do this subtly, as if you are bored or trying to be polite.
Make sure the person you have your eye on does not have a Valentine! Many people make the mistake of not asking their proposed Valentine if they have a date and cause themselves unnecessary embarrassment later on!
Make sure they would be willing to have a Valentine. If they go on and on about how they wish they could have a Valentine you can casually say, “I’ll be your Valentine!” and all is well, but if they don’t mention anything at all, make sure they would be willing to have a Valentine. They may prefer to have the day to themselves or already have a date.
Make sure they will be able to go on a date. If they are away on Valentine’s Day, then you cannot really have a Valentine’s date. However, you could ask them out in general, or go out another day.
Enjoy it! Valentine’s day is meant to be for you to enjoy! Do not get nervous, however hard it may seem, and try to not get sweaty as this is a big turnoff!
Whatever you do, make sure you don’t ditch them if they accept to be your Valentine. This will reduce the chances of you ever going out, ever.
Always be yourself. Do not try to change yourself to make someone like you. If they do not like you just move on to the next.
Some media groups have dating programs for the lonely so just go to some tv or radio stations to pool in possible dates for valentines.
Make an effort. If you are dressed as a tramp and she is a high-class make-up and heels kind of girl, she will not be attracted to you, unless that is the kind of person you know she goes for.
Always ask them to choose the destination first. This is good manners and will impress. If they can’t decide, and only if they can’t decide, you can choose.