I met a guy a few weeks ago at a party, and we hit it off. We have a lot in common, enjoyed chatting, and decided to meet again on our own. Since then, we have gone out to dinner a few times and have maintained a steady conversation online. I really like him and told him that a few days ago. He said he was flattered but would not get into a relationship because he wanted to stay single. I was hurt, of course, but told him that I understood and would like to stay friends. Is this a waste of time for me? I am in touch only because I am hopeful that he may change his mind. Should I date someone else to avoid getting hurt?
Is this person of importance in your life only if you have a romantic relationship with him? Is there nothing positive about him being a friend, given how much you enjoy each other’s company? You have both been honest with each other, which is commendable, so what you choose depends entirely upon whether you are okay with either scenario. He may change his mind, or he may not, and you have to accept both possibilities like an adult. If you can, you might find yourself with a friend. If not, and you can’t imagine anything other than a romantic attachment, you can walk away. Make your decision with your eyes open, to avoid turning him into the bad guy a few months down the line. 

My boyfriend said he would consider marrying me only after speaking to a lawyer to safeguard his financial interests. Is this a red flag?
It’s an indication of who he is and how he separates his personal life from his economic assets. If that aspect of his personality is opposed to yours, it’s a red flag. If it isn’t, and you can accept that he doesn’t evaluate this relationship in the same way you do, you should be able to accept what he proposes.