I’ve been wanting a serious relationship and using online dating ever since I saw a very convincing Oprah episode after college. I’ve met some wonderful guys online and even squeezed out a few relationships. But those are not the encounters I want to tell you about. I want to share my most horrible dates with you so you’ll be prepared when it’s your turn.

Date 1: The Drunk Driver

I met a guy on Tinder. Sure, he was unemployed and still living with his brother –  at the age of 32, but he was hot. I thought one date wouldn’t hurt. He arrived 30 minutes late but was really apologetic, so I brushed it off. We ordered beers, which I sipped and he chugged. In a period of 1 hour, this dude ordered 3 more beers, each accompanied by a shot of whiskey. Every time the waitress comes round, she didn’t notice my “save me” eyes. I’m was still on my second beer when he went to the bathroom and I managed to flag down the waitress to have her strategically bring the check. As we were saying goodbye in the parking lot, between sloppy attempts to kiss me, my date confessed that he was so nervous to meet me, that he had “a couple” drinks before arriving. When I asked if he was ok to drive home, he said he would sleep it off in his car. “It’s ok, I do this all the time,” he said. “Great!” I thought deeply deeply to myself.

Date 2: The Liar

I was getting sick of the casual Tinder encounters and decided to step my game up this time on Match.com. So when I was about three weeks into chatting with Joe, I wasn’t surprised that he seemed more serious than other guys I’d met online. He spoke a lot about his friends and his family and his job; he was an open book. Once I felt comfortable talking to him, we met up at a bar on one particular Saturday night, got drunk, and yes, I’ll admit it- kissed quite a bit. He asked me if I’d like to see him again – “of course, I would” I replied. He went out of his way to make a comment that he’s never used Facebook, but could give me his phone number. That statement just felt out of place- I wasn’t buying it. I went home and did a little amateur Facebook stalking. Surprise surprise, he did indeed use Facebook…and so did his girlfriend!

Date 3: The Kind-Of Catfish

I had finally found one: a guy who was charming, and incredibly handsome. He was a hockey player with a nice body. After a few weeks of flirty back-and-forth online, we moved our chats to the phone. Our conversations flowed so naturally, I felt like I was really getting to know him. When he finally asked me out, I couldn’t wait! As I pulled into the parking lot of our date spot, I gave him a call. He said he was sitting out on the patio, but when I looked around he was nowhere to be seen. I called him again, and saw an unfamiliar man in the corner answer his phone. It was too late to turn away; I had been spotted. As he walked over to me, I noticed he was about 5 years older and about 50 pounds heavier than his photos. “Ok,” I thought to myself, “I can look past this. It’s no big deal.” However, it was a big deal…to him. He knew that I knew that he had lied. He was so consumed with wondering if I accepted the real version of him that he couldn’t make eye contact and he couldn’t make conversation. The guy I had been talking to didn’t exist in real life. So I said “screw it”, ordered a pizza and stuffed my face because that was the only thing I could do to make my night not suck.

Date 4: The Threesome Seeker

It was a Saturday night and I was out with some friends when I decided to casually invite a guy from Tinder to stop by. “Tinder” guy showed up and introduced himself to the group like a gentleman. He and I spent a while playfully chatting over drinks. It was going well, until we decided to join a game of pool. I appreciated his social energy- chatting with my girlfriends. And then he was REALLY chatting with my girlfriends, but one in particular. This girl was more of an acquaintance. She knew I was on a date with him, but that didn’t stop her from hanging all over him. Eventually, he and this girl went outside for a smoke and when they came back, he asked me to ask her to have a threesome with us. And that’s how I went from date to “wingwoman” in about an hour flat. You can also guess which girl he went home with that night. Hint: it wasn’t me.

Date 5: The Ambush

Using a free dating site like OkCupid means that anyone can message you at any time. I replied to a message from a guy whom I wasn’t particularly interested in because I saw that we went to the same university. But the conversation fizzled and I hadn’t responded to his last few messages, simply because I just wasn’t interested enough to respond. Then, one night, I was out with some new friends in a new town and I saw a guy swiftly approaching the group. He interrupted our conversation with his phone in his hand. He flipped it around to reveal my OkCupid profile and asked, “Is this you?” Through my shock and embarrassment, I realized it was the same guy who I’d been ignoring. He wasn’t angry but I could tell that his social skills were a bit off. To make matters worse…he was with his girlfriend. Apparently, they had some sort of open-relationship. After my friends passed around this strangers phone to swipe through my profile, I went home and immediately, took down my profile.

Online dating can be a hit or miss. Sometimes, there really is no way to know of knowing what someone is hiding until they’re right in front of you. I‘m not discouraged by these bumps in the dating road – if anything, these dates have kept me realistic. It’s all about chemistry…and life choices. The biggest lesson I take away from all of this is never settle for anything less than sober and sane!

Dana Simmons
Dana was determined to find that special someone. Years of being single made her reluctant to believe salvation would come from the online environment. Now a married woman and a mother of two, Dana’s an advocate of online dating sites and is passionate on writing about their success. Dana is a regular contributing writer to the Top 5 Dating Sites blog.
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