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Fourth time wasn\u2019t the charm for Nick Viall<\/strong> <\/a>\u2026 but he makes for an entertaining Bachelor.<\/p>\n Bachelor Nation first met the Wisconsin native during Andi Dorfman<\/strong><\/a>\u2019s season 10 of The Bachelorette,<\/em> which aired in 2014. After finishing as the runner-up, Nick returned for Kaitlyn Bristowe<\/strong>\u2019s season 11 of The Bachelorette.<\/em><\/a> He subsequently made history when he came in second place for the second time. While Nick and Kaitlyn had a rocky<\/a> relationship after she accepted a proposal from Shawn Booth,<\/strong><\/a> he proved they were back on good terms when he joked about his proposal airing on the Bachelor: The Greatest Seasons \u2014 Ever!<\/em> in June 2020.<\/p>\n \u201cIt was like waving at someone who\u2019s waving at the person behind \u2026 but million times worse. TBH I look back on this time of my life and have nothing but positive memories,\u201d he wrote via Instagram. \u201cI just didn\u2019t think ABC would make us relive the entire failed proposal tomorrow night \u2026 It really was a season for the ages. You never know how you view things as time passes. Glad to be able to call KB a good friend!\u201d<\/p>\n While Kaitlyn and Shawn called it quits in November 2018, Nick went on to appear on Bachelor in Paradise<\/em> season 3. After forming a connection with Jen Saviano<\/strong>, Nick opted to leave the beach solo and fans were shocked when ABC named him the season 21 Bachelor.<\/a> And while he found love with Vanessa Grimaldi<\/strong><\/a>, they called off their engagement several months after the 2017 finale.<\/p>\n Three years later, Nick reunited with several of his contestants to record Patreon<\/a> episodes of his podcast.<\/p>\n \u201cSeemingly those childish antics I cringe watching back, [but] it was great TV,\u201d Nick said during an episode with runner-up Raven Gates<\/strong><\/a>, opening up about the \u201csex narrative\u201d from the show. \u201cI was fine with the edit, but it\u2019s hard for me to watch back.\u201d<\/a><\/p>\n He continued: \u201cEven with Vanessa, we didn\u2019t work out, but I was going to pick her. That\u2019s who I fell for. I was nuts about her and I have no regrets about stuff like that. I had a hard time letting go and enjoying. I felt so responsible for everyone.\u201d<\/p>\n