I Thought I Knew Him Until I Snooped On His Computer

My boyfriend and I had been dating for six months and things were going well. We spent most of our time together and had even discussed our potential future together. I actually thought he might propose soon and while I had my reservations, I thought I knew him well enough to say yes if he did. Unfortunately, I discovered the opposite was true when he let me use his computer one night. I didn’t mean to snoop but once I started, I couldn’t stop.

  1. I found a few gambling sites he’d used. Gambling certainly wasn’t a deal breaker—a lot of people, girls and guys, gamble online. But how much did he win? How much did he lose? Was it a problem that would make a difference financially to us if we ever got married? The subject of gambling never came up in prior conversations and I couldn’t exactly bring it up, but it still played on my mind.
  2. He had a DUI a couple of years before we met. I’m not against any boyfriend or possible-fiance drinking now and then, especially since I love to indulge in a glass of wine occasionally at a dinner party or from the comfort of my couch. My guy was a social drinker, but was there more to it? It seemed so. He’d never mentioned that he got a DUI and I started to wonder if he had a secret drinking problem I knew nothing about.
  3. His search history was full of debt consolidation sites. I was beginning to feel uneasy about his financial situation, which was a topic we’d never discussed. Was he in debt? How much? He seemed to have no problem paying his rent and other bills and he had a good job as a real estate agent. He even insisted on paying for my dinner or movie ticket each time we went out. But what if it was all credit card debt? Was this a serious red flag?
  4. He’d bookmarked a bunch of dating sites. Of course we’d both dated before and generally speaking, we were both open about our past relationships. However, he never mentioned that he’d dated online. This made me wonder if he still used the sites and had active profiles on them or if they were old bookmarks he no longer used. I thought he was a trustworthy man, but now I just didn’t know.
  5. He was estranged from his family. I’d never introduced him to my family because they lived on the opposite coast, but after I found some email exchanges with his mother and brothers, I realized why he’d never introduced me to his even though they lived an hour away. He had lots of hard feelings toward his mother after she divorced his father since he’d died of heart failure not long after and my boyfriend blamed her for his death. He told her this regularly in emails and his two brothers defended her. I didn’t have all the facts, but I had no idea his family situation was so messy.
  6. He searched for and contacted a lawyer about a prenup. OK, so maybe he was closer than I ever thought to proposing, but I was VERY insulted by the idea of a prenup. Call me old-fashioned, but my ideal marriage was the 50/50 route. The thought of signing a legal document instantly made me feel like he didn’t trust me or that maybe he thought I would take him for everything he had should we ever divorce. Plus, it also made me think he had more money than I thought he had and that he wanted to hide his finances from me. Maybe he won the lottery! Ironically, it made me suddenly want a prenup too. We never really talked about money and I started to realize we should have.
  7. He wrote a love letter to his ex-girlfriend. Sure, it was via e-mail and it was still in his Drafts folder unsent, but it sure was heartfelt and full of emotion. It made me suspect that he could still have some feelings for her. Some sort of closure was needed, right? Why hadn’t he sent it? Why hadn’t he deleted it? Why did he feel the need to write it in the first place? He’d written it a few weeks after we’d met. We’d never discussed her or his feelings about her so this was awkward and infuriating, to say the least.
  8. He’d made a sex video with the same ex… and kept it. I was about to blow my stack. Our sex was good, yet he hadn’t asked ME to do a home sex video with him. Not that I would, but it’s nice to be asked, right? On the bright side, maybe he thought of me more as the future mother of his children than an exhibitionist. Yes, I’m sure that’s it.
  9. He owned a whole lot of porn. I know guys like to have their cheap thrills now and then, but my boyfriend’s hard drive was LOADED with porn. Alarm bells went off and didn’t stop, even after I stood up from his computer, closed all his tabs, and stepped away to catch my breath. I began to doubt myself. Wasn’t I enough for him sexually? Was he going to do this throughout our marriage? Should I just let it go?

These things weren’t deal breakers individually, but when I added them all up, there were problems that weren’t easily solved. I tried bringing up the things I wanted to discuss but he was really evasive and said I needed to focus on the two of us and our future together. I broke up with him, confessed that I’d snooped on his computer, and would only reconcile when he was ready to be honest and talk through some things with me. That still hasn’t happened.

A freelance writer, photographer, and artist who lives in Ky. Love cooking, baking, and spending time with family and friends.