How do I know if I am really in love with someone? There is a guy I meet quite often, and I enjoy spending time with him, but I can’t tell if I should get into a relationship with him. We have common interests and I know he likes me even though he has never said anything directly, but I never discuss this because I can’t figure out what I want and if I should keep seeing him. This has been going on for almost two months and I’m sure he’s confused but if he doesn’t say anything either, it feels as if we are drifting towards a friendship and I don’t know what to do about it. Is there a sign that this is supposed to be more than a casual friendship?
If neither of you feels the need to discuss where this is going, why not sit back and enjoy getting to know each other? There’s no pressure or compulsion for either of you to qualify what kind of relationship this is and, sometimes, allowing a friendship to evolve into something else has its own rewards because there is a greater level of understanding. If you don’t know what this is, that is perfectly okay. Keep meeting whenever you both like until one of you feels the need to try and get some clarity. When that happens, it will be easier for you both to figure this out together because there will hopefully be a greater level of comfort. Until that happens, don’t be too hard on yourself and don’t worry about signs.

How can I convince my boyfriend to take the next step and discuss making our relationship a more permanent arrangement? I want to settle down but I don’t know if he’s ready.
You won’t know until you ask and the sooner you can talk about your expectations, the easier it will be for you both to get a sense of where this relationship is heading, and if it is in the right direction.