[He's mildly amused by this person. He loves chess and therefore sees no problem with arranging it. He probably wants to assess him but -- Ciel wants to assess this person too.]
Love is weakness as far as I am concerned in that light. However -- simply because it does not work for me or worked for my parents does not mean it is not going to work for others. This isn't to say I'm encouraging you. Do not forget that my perspective on it won't change.
It wouldn't surprise me at all if they did. Some people simple don't have self control or control over their emotions or thoughts. What they think is 'love' often times is just blind infatuation.