Get to know her. Do some research -- but not too much People are going to Google each other and that's OK, but don't go overboard with your background checks. Be more online dating sites approachable. This is not a typical relationship and has to be handled differently. Girls, we all been there. For example, if you've just cracked that joke and she's laughed, at least be ready with a line like And so, what are your thoughts about X,Y,Z, or, What do you like about your job?, etc. You also recognize social niceties; that is, what sort of effort he makes to ask you questions, whether she is constantly checking her phone, etc. It's a very sick world How to Date Your Neighbor. You'd be surprised how often dates turn up without showering. Act like nothing happened if they ignore it, but yet act serious with them. Give a sipper. You're a lean, mean, guy-picking-up machine; there are other fish in the sea, so go get 'em. is another nice line. The hard part is deciding which one is for you. This will give you insight into the seriousness of the situation and the steps that need to be taken. Don't force your smile. Maintain neighborly proximity. If he or she says no to you initially, avoid a self-indulgent pity party. It's key to read between the lines to get a sense of whether the person seems well-adjusted - pleasant, friendly and reasonable, someone you would be drawn to if you met him or her in person, even if you didn't know her top five favorite movies. It doesn't need to be long at first and it definitely shouldn't be complicated or make your partner feel uncomfortable. Don't underestimate the competition, although you have the advantage because you actually know about her. Be yourself. Let them get used to you not being there for them at all times. Being funny is innate, provided you trust your sense of humor to shine through. Practice being funny. Keep yourself simple. Sorry to tell you but men love women who can look after themselves, who aren't needy. Don't start worrying about what disasters could happen, because that way they are far more likely to.