I don’t know why my boyfriend has to pretend to be tough all the time. It makes him very unreasonable because he has this delusional idea that he has to be in control of our relationship. It’s toxic masculinity and it is getting in the way of making this relationship stronger. He is a loving and kind person, and I know he has the potential to be a better, more secure partner, but his inability to break out of this space and confront who he really is often makes me wonder if he will ever be mature enough for me. Should I keep dating him until he comes to see this from my perspective, or write off this relationship if he can’t stop playing the role of ‘alpha male’?
The ‘manosphere’ is a problematic space and any relationship that doesn’t acknowledge its impact can fail in all kinds of ways. You’re right to think about his maturity here because it’s obvious that he isn’t approaching this relationship from a perspective of equality. Some people may like the idea of someone taking charge, but many others prefer equal rights. If what is happening here isn’t aligned with your expectations, you should call it out and insist on change. If that doesn’t happen, ask yourself if being kind and loving is enough for you. Also think about how long you are willing to wait until things change.

My boyfriend describes himself as a ‘womaniser’ and says it’s just harmless flirting that shouldn’t bother me. He says he is being upfront about it because he doesn’t want to pretend and is okay with me ending this relationship if it’s a problem. Am I being prudish?
No, standing up for yourself and demanding respect for yourself as well as for other women isn’t prudishness; it’s essential and important. If he doesn’t understand this, he isn’t someone who deserves to be in a relationship and you are belittling yourself by being in this position. Think about what you are being asked to condone.