Success rate is also affected by your character's skills. With each dialogue option you will notice a percentage chance of success - of course, choose the ones with the highest values.
If the relationship with the character is at least 0 (it cannot have a negative value), a dialogue will be initiated during which you must answer three questions correctly. When you get to the beloved character, talk to him or her about starting a family in the future. This is important because if you fail during the conversation, then you will lose the chance of marrying that particular character. Before talking, it's worth saving the game - if the dialogue fails, you can load the game and try it again.