Ashley Olsen appears to have a certain fondness for gentlemen with some life experience under their belts. In 2016, after her brief romance with director Bennett Miller, Olsen was spotted getting cozy with artist George Condo at Balthazar in New York. "It was obvious something was going on," an insider alleged to Page Six. The pair was reportedly spotted cuddling and holding hands just like a couple. Additionally, the source declared that the age difference between the pair was quite noticeable, with the insider saying that Condo, who was 58 at the time, looked like he could be Olsen's (then 30) grandfather. Previously that year, the outlet had speculated that there were sparks between Olsen and Condo; however, reps for both individuals insisted that the pair were simply having a work meeting.
Nevertheless, as noted by the Daily Mail, Olsen's aforementioned dinner with Condo seemingly indicated that the pair were involved in more than just business. Likewise, People noted that during the pair's dinner, Olsen and Condo were seated in a secluded booth typically used by couples.
In a 2016 exclusive, Condo's ex-wife, Anna, told RadarOnline she wasn't thrilled by the idea of her former husband dating Olsen. Anna claimed that before the rumors started, she and Olsen had been friends. However, Condo's ex also admitted that she didn't know if the speculation that her ex and Olsen were dating was true.
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