So how many women have you been with? 
I’ve dated 4-6 girls when I was in HS/College and earlier on when I started working; and have met over a dozen ladies in XXX the last decade or so.  I travel a lot and have met other ladies in other cities but they really don’t count as it is hard to maintain even a casual relationship when you are flying in and out of a city.
What do you do to pick up women? Have a special technique, play on their insecurities, are a nice guy… do you pick up women on line?
No, I don’t have any techniques – I tell them exactly what I am about.  Unless being a nice guy/gentleman is a technique (that’s one’s breeding, so I won’t consider being a gentleman a “technique” per se).  In one of my first dates, the lady walked out as I had used an older pic of myself (in my defence it is tough for guys to have good pics as we are not proned to taking massive amount of selfies, etc. but I’ve since invested in some recent and professionally taken pics).
I have two dating persona – one for the ladies interested in just casual encounters for fun and kink (I am a shibari master and these ladies are aware of what I am about with rope play), and another for longer-term relationships.  Most of the ladies I’ve dated in XXX I’ve met on-line on CL (I mostly respond within the “Casual Encounters” or the “Women for Men” sections, for the two categories of ladies I’ve met, respectively).  I travel a lot and I am equally up front with the ladies I’ve met in other cities.
P/S:  Never play on a lady’s weakness or insecurities … or anyone’s for that matter.  That’s evil, and desperate.
What are the biggest challenges when dating multiple women
When one lady slowly becomes serious and you have to figure out a way to phase out of the others.  This is not an issue with casual encounters … the more the merrier in this case (although when I am in a LTR, I do not meet others casually).
Are you looking for something more serious ultimately and if not/ yes, why?
Can’t really look for anything serious as that is really presumptious … when it happens it happens.  However in one case, it developed into a LTR, for 2 very nice years before we broke up.
What’s the craziest experience you’ve ever had while dating?
From my Casual Encounters persona, rope bondage (this I had always explored, way before 50-shades made it popular).  Rope bondage may sound rough and painful, but it is all about mutual power exchange.  I am engaged in a more ceremonial form of rope bondage (tea ceremony included) that is slow and easy, sensual and intimate … before it gets intense as each lady has a different threshold for intensity.
The nicest?
The 2-year LTR.  It was an awesome relationship where we were both honest with each other’s wants and needs and us making changes in our lives to accommodate each other.  We had a very intimate/sensual relationship for two solid years before it ended abruptly (we couldn’t reconcile my travels and my love for ropes).
How old are you? 
Early 40s.