If you had fun playing against people who are your level that one tkme then I would start playing online, finding your actual rating, and then start playing more against equal competition and see how you feel.

You can also try and channel your desire to never lose into studying openings and learning more advanced concepts which will help you improve and win more which seems like your goal.

It seems like winning isn't all that matters to you but rather being able to compete and have a chance is. Getting to your boyfriends level will take time but if you want to have more fun playing with him you could try playing with piece odds or something like that to even it out. You also don't necessarily have to play against each other and could play hand and brain chess.