How can I make him date me?

There are so many red flags here that I suggest you think carefully about why you like this person and what you hope to get in the rare event that he decides to ask you out. Will being with him lead to any satisfaction based on what you want out of a relationship

I’m interested in a guy who only wants to date someone who is already dating. He thinks there is more pleasure in making someone break up and then date them. Unfortunately, I am not dating anyone. He has asked out a lot of girls who are dating but has never asked me out. We are very good friends and I try a lot to speak to him, but he does not reciprocate. What should I do?
— MC
I’m not sure what the attraction is here, given how obvious it is that this is a fairly troubled human being. The idea of only asking someone out if they are dating is disturbing on so many levels. If he hasn’t asked you out, it’s safe to assume you dodged a bullet here. Also, when you mention him asking a lot of girls out, the implication is he is unable to maintain a steady relationship with anyone. There are so many red flags here that I suggest you think carefully about why you like this person and what you hope to get in the rare event that he decides to ask you out. Will being with him lead to any satisfaction based on what you want out of a relationship?

My friend and I have decided to get into a relationship if we are both still single at 30. Is this a good idea? Should we be wary of anything before getting into this kind of arrangement? Will it damage our friendship?
Arrangements like this sound great on American sitcoms, but need to be examined in the cold, clear light of day. A relationship involves feelings, which can’t be forced. There are obvious advantages to dating a friend, but you should both be aware of how the nature of your friendship will change irrevocably the minute you decide to turn it into a romantic relationship. I suggest you examine the risks and consider any possible awkwardness or harm to your friendship if things don’t work out, before setting down this path.

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