I’ve dated all of the wrong men (so you won’t have to!)


Hi. I’m the lesser known Taylor Swift of dating. This year marks my second decade of dating!  I know how exciting this is, and you’re welcome to throw me a party to celebrate (please feel free to bring along some wine). It’s been an interesting twenty years, and I’m going to drop some wisdom on you about the different types of men out there (and who to stay away from). Let’s jump in, shall we?

The Marrying Guy – Sounds great, right? He has always wanted to get married, and talks at length about the life you will share together after you’re married. His parent’s have been married forever, and he had an upbringing that is something out of Leave It To Beaver.  One day he starts talking about what he expects from you as a wife, and buys you an apron as a Christmas gift. Before long you are being forced to convert to his religion, because his parents couldn’t handle it if your children weren’t raised in the church of their choosing. Have I mentioned that you’ve been dating for only slightly over a year. Also, get ready for a real snooze fest of sex (yawn). Maybe this sounds like the perfect man for you, and if so, I’m happy to give you his number.  Being a 1950’s cardboard cutout of a woman just wasn’t in the cards for me.

The Nice Guy – We’ve all met him, and we’ve probably all been confused by the fact that he’s kind of an asshole. He talks ad nauseam about how nice he is, how much he does for other people, and how he doesn’t understand why he can’t just meet a nice girl. He’s also moderately predatory with his brand of niceness: showing up unannounced at your home and place of work, making you feel as though you owe him something in return for his niceness, trying to force intimacy, and wanting to look you in the eye during sex (the whole time). Slowly but surely his true colors start to burst through like a fucking rainbow, and he starts saying things like, “I just can’t stay away from crazy”, or “My sister is so much nicer than you.” It turns out that Mr. Nice Guy has the same mentality of a high school football player who has taken a girl on a date, and has just been told that she isn’t having sex with him. When you eventually break up with Mr. Nice Guy, he goes ballistic; screaming and yelling things at you that you could never have imagined coming out of his mouth.  Beware of the ‘Nice Guy’, he’s probably an asshole.

The Band Guy – I’ve taken more than one trip down ‘musician alley’, and while these guys are inherently sexy and mysterious, they should carry a huge waring sign that reads: YOU WILL BE CHEATED ON.  I’m not going to tell anyone not to go the way of the sensitive musician at least once: they are hot, they are good at expressing how they feel, and you’ll probably have a song written about you. Everything I just mentioned that sounded like a positive, are also major negatives. They are hot (other women notice this too, and don’t care if your music man is already spoken for), they are emotional (seriously, it’s like dating a woman), and you’ll probably have a song written about you (there’s a good chance it won’t be a very nice song… trust me, I have an entire album dedicated to how terribly I broke someone’s heart). Every woman needs to experience this once in her life, it can be a total blast. Heed my warning though, it will not end well for you.

The Sexual Deviant Guy – I’ve come across quite of few of these fine men in my time. I love a good deviant roll in the hay as much as the next gal. However, sometimes you find someone whose sexual kinks end up taking the staring role in your relationship. If you love threesomes, this is your guy. If you love S&M, this is your guy. If you love exploring your bisexual curiosities (or his), this is your guy. I love this sort of thing, but be warned that your relationship will end up revolving around sexual deviancy. Oh! If someone tells you that he’s a sex addict, take it as gospel; he’s probably telling the truth. Again, be prepared to be cheated on. Your type of situation? I don’t judge. I wish you more luck than I’ve had with this sort of guy.

The Virgin – Unless you yourself are also a virgin, and the two of you are planning to lose your virginity to each other… don’t ever, ever, ever date a virgin (or otherwise sleep with him). He will fall in love with you, it will be painful and sad, and you will feel like you need to physically rip him off of your person to get rid of him. There is just no room for error in this situation: if a man is a virgin: run.

The Really Religious Guy – Full disclaimer here, I self identify as a Lutheran who doesn’t follow the rules of the church. I pass no judgement on those who are religious, I only aim to say that a dating situation with two people who are ‘unevenly yolked’ (that’s in the bible btw) is a potential disaster.  I dated a ‘band guy’ who was a ‘virgin’ and ‘really religious.’ Some of the strangest moments of my dating life took place in this relationship.  Being sexually repressed all of those years did something to this poor guy; when we started dating it was as though he was trying to play a game of ‘catch up’ for every sexual thing he had never done before. I ended up with multiple UTI’s because he felt the need to shower before and after any sexual contact (while rubbing soap all over me and asking me if I was a “dirty girl”).  I enjoy and embrace being sexual, but I literally couldn’t spend five minutes with this guy without him groping me; it was exhausting. When we finally had sex for the first time it was in a bunk on a tour bus (classy, I know), and he cried afterwards and asked me to pray with him. I thanked God that it was dark enough for him not to see the look of horror on my face. Oh. And his mother was strangely involved in our relationship, and reminded him that we should never share a hotel room together, because we were not married. Guess the bunk of a tour bus was okay though. Unless you are religious, just don’t date the ‘really religious guy.’ It will be weird, you will get a UTI, and his mom will be peeking in to make sure you’ve made ‘room for the Lord.’

The Older Man (bonus points if he’s in his forties) – Do you enjoy difficult puzzles? Ones where as soon as you’ve found where a piece should fit, the ends up morphing into something else? Do you enjoy mental gymnastics? Does all of this sound like your idea of a good time?  Great news… I’ve found your future husband! He’s older than you, probably been married, maybe has children already, he’s successful, and he’s a self proclaimed ‘eternal bachelor.’ He seems self assured, as though he’s really grown to know who he is and what he wants. He seems confident, he’s good looking, and he does a really good job of sweeping you off of your feet. Perhaps it seems as though he is the person you’ve been waiting for your whole life; he is the husband you pictured when you were a young girl. Boy do I have news for you… he’s not. Once he has you, things change really fast. Suddenly he speaks in prose, you’re never sure what anything he says actually means, he’s aloof, he’s emotionally unavailable, you’re never really sure what he’s doing, and he’s not ready to settle down. There will always be other women around. You’ll never be able to pinpoint whether they are just ‘friends’ or whether he is sleeping with them.  Ladies, if this sort of headache is your cup of tea, find a man in his forties! Let me know how it works out for you.

Dating is tough. Good luck to all of you out there who are doing it right now. It’s a crazy adventure that ends up with a lot of cautionary (albeit funny) tales.




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