I went on a date around a month ago and had a good time, but not a great time. It felt like the guy was decent but not very interesting, so I didn’t message him and assumed this wasn’t going to go anywhere. A few days ago, he called to suggest another date and I agreed, but I don’t know if this is worth pursuing. If I meet him again, I worry that I may be giving him the wrong impression. At the same time, it feels rude to dismiss him after just one date because it’s possible that we just didn’t know each other well enough to find common ground. Should I keep seeing him until I know for sure?
It’s possible that you’re overthinking this because neither of you knows where this is going. If you don’t like spending time with him, you are under no obligation to meet him and are not being dismissive in any way. In fact, it is better to avoid meeting if you’re not optimistic because that prevents any misunderstanding or awkwardness. Meet him again if you’re curious and be firm about how you feel if the conversation continues. Prolonging the inevitable is a waste of time for him as well as yourself.

My ex-girlfriend and I broke up around four months ago. We have begun chatting again and I feel as if we may try giving our relationship another chance. I also know that she has been on a few dates with someone, so I don’t know if she is still making up her mind about what to do next. Is a second chance risky, given that she may be interested in another guy?
How do you feel about a second chance? If you both want this to work, the presence or absence of someone else is irrelevant. Think about what went wrong and whether you want her in your life. If she is important to you, and you want to be with her, nothing else can or should matter.