Should I contact last year's lover?

Hi everyone. I’m thinking of contacting an ex. I guess he is not really an “ex” since we were never officially together as in referring to each other as bf-gf. We met last year around this time and he chased me like crazy but I wasn’t interested. After finally giving him a chance I got hooked. He was so much fun and we had a really great summer. He had such great things to say to me and made me feel wonderful. The problem was he had only been divorced 5 months and his ex wife was still causing a lot of drama in his life. I found it hard to deal with since it turned him from the happy-go-lucky guy I first met to him being preoccupied and stressed. So I ended it last September. Now that summer is coming I keep thinking of him and how much fun we had. I thought of maybe sending a text to say hi and that he’s welcome to come hang by my pool with his daughter like last year. I guess the scary part is that I know I have feelings for him. I started to really care for him and his daughter and although he treated me really well and said amazing things I found that he was somewhat closed off to the idea of a relationship. What do you think, should I get back in touch or not? Any advice is welcome and I’d love to hear a guy’s point of view of this – would you be happily surprised or annoyed?