Should I explore a new relationship?

I am a 44-year old woman and have never married. I was in a long-term relationship in my twenties that didn’t work out because my boyfriend at the time broke off our engagement and I never got over the heartbreak. A few months ago, a colleague of mine at work began asking me out to dinner. I agreed because we have known each other for many years and he has always seemed like a nice, kind person. When I got to know him better, I found out that he has been divorced for a year and has been interested in me for quite a long time. I was flattered, but he also makes me nervous because I have not been in a relationship with anyone for almost 20 years. He wants to be with me, but I am afraid. How do I know if this is a good idea?
You won’t know what it is unless you make that leap of faith. Start by asking yourself what your feelings for him are, and whether you like spending time with him. Don’t let the idea of a relationship loom over anything because all you need to do is get to know him better, without the pressure of it needing to lead to something. Meet him whenever you’re comfortable, get to a space where you are okay with speaking your mind, and then worry about whether you will be able to manage a relationship after all these years. We are social beings who respond to kindness and companionship. Years of being single can disappear in an instant when you’re ready to be with someone.

How can I convince my girlfriend to dress more appropriately when she comes to visit me at home? My parents always disapprove of what she wears but she doesn’t seem to care.
Why should she care about what your parents think she should wear? All that matters is how comfortable she is, given that it’s her body and her clothes. The adjustments should come from you.