Probably he was big into the whole Jedi shit. Of all the Jedi he's the most tryhard like he fucking loved it. He really went balls deep with the whole jedi thing. Probably never bothered trying to chase girls he was so happy with that shit.
Probably got laid on Tatooine tho to be honest I can easily see him being shit with women since he probably only ever talks about Jedi shit so when he was in hiding he probably had almost nothing to say or just let on he was a jedi obsessed autist.
That said with the face of Ewan McGregor none of that fucking matters he probably got laid alot.
TPM Obi Wan especially has the jaunty smirk of a guy who fucks whoever he wants.
Probably up through Episode 3 but after a few years of sitting in the desert counting grains of sand and fucking with Sand People pretending to be Krayt Dragons, he probably got bored and decided the Jedi were dead anyway, May as well bang some chicks.
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