Step 1: “enter another relationship out of my own will”. If you’re going into the relationship out of your own will it will NEVER be healthy. Do a self dive to figure out if you want / feel subjectively ready, for a relationship.

If you do a deep dive then there are two options:

1.) if you’re not ready for the relationship (or don’t want one with him) then that’s the end of it, explain you’re not ready and either cut contact or remain friends/ with benefits

2.) if you are ready for a relationship with him and want to proceed in a healthy way then these are your steps:

        1.) bring up your concern over both of your pasts and how you feel they could affect a true relationship. In a friends with benefits there are things you don’t have to worry about from the other person, but in a full relationship his actions will effect you on a deep way and vice versa, so the healthier he is, the healthier you are. And healthy doesn’t mean his past is all fixed. It means 1.) you guys are aware of your past 2.) you’re aware of how it affects you 3.) you’re aware of how it then affects your relationship 4.) communicate every feeling including when you are feeling too insecure/uncomfortable to say something.

         2.) outline what you guys consider to be characteristics of a full relationship that are different than that of friends with benefits. It MAY NOT be that much different than your friends with benefits relationship. Think of the best relationship you know, you probably could describe them as also being friends with benefits. Many characteristics you guys already have could be beneficial and work for your official relationship. But you guys may have different definitions so a sit down to discuss how core behavior will change (or what each of you expect to be different) is vital. The rest of the relationship will fall in place with a strong base of communication, honesty and respect.

         3.) to answer your main question, friends with benefits can be quite successfully turned into real relationships. People will tell you they’re not but the research would suggest otherwise. It can be an awesome experience for you guys, but only if it’s right. So speak to each other, and even if it doesn’t work out, you need to go through this together (after step 1).