I Dated A Guy Who Was A Millionaire — Big Mistake

Dating a successful millionaire was like living in a fairytale… while it lasted. He was well known in Manhattan and I was the struggling writer trying to make it in the big city. We met one night in the city after matching on Tinder and little did I know that he was going to be one of the hardest people I’ve ever had to walk away from in my life. Here’s why it ended:

  1. He Was Still Married. First red flag of the many that I should’ve acknowledged immediately was that he was still technically (and by law) married. Yes, they’d been separated for almost four years, but his wife never signed the divorce papers. Having kids, real estate, and bank accounts all intertwined apparently was too overwhelming for his wife to handle, hence the no signage.
  2. He Was Never Going To Commit To Only Me. Not only did his friends tell me that he was trying to fix his marriage, the guy himself often told me he was over her and ready to “play the field,” which… what? I knew deep down he was never going to only be with me. It hurt too much to think that I wasn’t the only woman in his life.
  3. He Was Scared Of Falling In Love With Me. Without having to tell me, I figured out that he was scared of being with me. He knew I was perfect for him and after so many all-night conversations, he told me he feared his feelings for me. It warmed my heart to hear that he was in love with me, but it broke my heart down the road because he never did anything about it.
  4. I Was Always Going To Be A Secret. I knew that I was never going to meet his kids or spend any holidays with him by my side because he was too wrapped up in his “old” life. I would only ever be the quick phone call to come into the city and spend the night in a hotel room or a late-night FaceTime when he was lonely in LA. That just wasn’t enough for me.
  5. We Spent More Time Arguing Than Anything Else. We argued through probably 95 percent of our phone calls and texting sessions. He didn’t listen to me when I told him that he never gave me a choice to be in his life. He basically made my decision for me. It was like talking to a wall because he wasn’t absorbing my words. Who wants to live like that?
  6. He Wanted Me To Fulfill All His Fantasies. In his mind, I was this perfect, well-behaved “mistress.” He never wanted me to complain or do anything that would mess up our “relationship.” When he wanted to FaceTime or send dirty pictures, I would stop what I was doing and get on my phone. I did it to myself every time but I hoped it would eventually pay off. Unfortunately, it never did.
  7. I Knew I Was Never Going To Be Totally Happy. I fit into his lifestyle well enough but I knew I was never going to happy. I was his dirty little secret and kept my mouth shut. I wanted him as my boyfriend or more and held on to my own fantasy with him. I didn’t care that he was loaded and always footed the bill because I paid in my company.
  8. He Was A Total Wimp When It Came To His “Wife.” He was a wimp not to put his foot down for his freedom when he first asked for the divorce. His estranged wife had him by the balls and wasn’t letting go. It’s been almost five years since they separated and it’s as if nothing has changed because he’s still accountable to her for everything he does.
  9. I Felt Like I Was Never Going To Be Good Enough For Him. There were many times he would post social media pictures showing off his lavish lifestyle. I felt like a plain Jane next to him. I didn’t have private planes and Upper East Side apartments so I felt as if I could never be anything more than that. Of course, looking back, I was the best thing that ever happened to him — but I definitely didn’t know that then.
  10. My Friends Finally Convinced Me He Was A Jerk. After months of interventions and point blank calling me out on my actions, I finally listened to my friends. They’d been telling me that he was never going to change for way too long but I didn’t listen. It hurt to finally admit that all my fears were coming true. Looking back, I’m fortunate for my friends opening my eyes. Having a sugar daddy certainly wasn’t all it was cracked up to be.
28-year-young writer with a love for reality TV, boy bands, Tinder, and being the most bad ass single lady on the East Coast.
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