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First off, Glad you are here. Those are some tough questions, but here's some random thoughts, just take them for what they are worth. #1. Only you two can truly answer that question. Everyone carries their own life experiences with them into swinging, whether that is a repressed background, prior sexual experiences, etc. It's part of who you are, and you can't totally change it. It not really a direct answer to your question, and it gets said a lot around here because it's key advice, but if you do decide to try, just take baby steps and ease into it going at the pace of the slowest person. Got to a club, and just plan on having a fun night together, nothing else. Talk about that, and if it was something you both enjoyed, then go back, again with no expectations. Just see how that goes and pretty soon you will know the answer that is best for you. Also, although swinging seems to be attracting the younger crowd too nowadays, it's always red flag when I see a younger couple who's relationship is relatively new too. It's always dangerous to project yourself onto someone else but I know that we would definitely not have been ready ourselves at the point you two are at. 2#. Again, only you two can decide, but be very careful here. Even many experienced swingers aren't comfortable with the playing alone scenario, and starting off that way is like strapping on snow skis for the first time and going right past the bunny slope to the black diamond. It may be great fun at the very first, but before you know it is totally out of control and not headed in a good direction. The fact that she suggested it makes it a little more viable option, but extreme care is still needed. 3#. Single men have a rough time in the lifestyle, not impossible, but not easy. You will have to work 10X as hard as you would as a couple, and your age isn't going to help either. Many people who are looking for single males want someone who is experienced, and by that I mean someone who knows what it is all about and aren't looking to just get laid. Being a couple but playing alone confounds things too since it is a unique scenario - even if she is totally ok with it, try to lie about it to avoid having to explain your situation every time, and you'll get sniffed out immediately and game over. The cheating husband wanting to play as a "single male" is common and most swingers want nothing to do with them. Like everything, swinging has it's own subculture and lingo, and if you don't know it, you'll get pegged almost immediately like most do. If you go this route, to avoid what I just described, in most cases she will have to be involved in setting things up. Sorry to be so negative, but that's just how I see things for you. All of that wasn't meant to say the answer is absolutely not, but just pointing out that you are going to be paddling upstream - difficult but not impossible. Good luck.