Dr Love with Mid-Day: Does this mean he wants to marry me?

A couple of days ago, while I was attending a friend’s wedding with my boyfriend, he casually mentioned shopping for rings. I was shocked but didn’t react at the time and have been thinking about that comment. Is it a hint that he wants to take this relationship to the next stage? I don’t know how I feel about that and am afraid to bring it up because it may be embarrassing for us both if he was just making conversation. Is it a sign that I am just not getting? What should I do?
You should wait until your boyfriend says something specific instead of jumping to conclusions on the basis of a throwaway comment alone. If he wants to say something about this relationship, he will, and there will come a time when you can both speak about that if and when it feels right. If you aren’t comfortable with the pace at which this is moving, you are allowed to change it because relationships evolve when two people work together. There’s no point overthinking this for now. Continue with the way things are, focus on getting to know each other better, and let this happen in an organic manner. Also, if you have questions and this is causing you anxiety, nothing stops you from just asking him why he made that comment. A healthy relationship is one where you can ask questions and talk about anything that is bothering you.

Should I pretend to be with someone just because he owes me money? I don’t want to be in this relationship but if I break up, I know my boyfriend won’t return what he owes me. I feel trapped.
Ask yourself what you are giving up in exchange for the money owed, and if the toll on your mental health is worth it. If you are with someone under false pretenses, it doesn’t help either of you. Try being direct about finances and where things stand because that will put you in a stronger position.