Category Archives: Horror Stories

Do People Actually Wear Christmas Sweaters on Dates? Yes, They Do

There are people who can pull off seasonal clothing, I think we can all agree on that. Babies, grandmas, little kids who get forced into it by their parents who want to take pictures that will subtly mock them for … Continue reading

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What Happens When You Date Someone Under 25

I get a lot of emails asking how young is too young to date. And, not surprisingly, most of these emails come from men. Ok, all of these emails come from men. So as a way of answering these “gentlemen,” … Continue reading

Posted in Horror Stories, Internet Dating is Weird | 8 Comments

Why You Should Never Take a Date to a Concert

I have a long held rule about taking dates to the theater. I love theater. And I love girls who love theater. But I found that every time I would ask a girl to check out the next big thing … Continue reading

Posted in Horror Stories, It's Not a Match Classic | 8 Comments

The Girl Who Was a Mennonite

Do you know what a Mennonite is? Neither did I. Mennonites, it turns out, are a traditional, peace-oriented religious group that can be like Protestants, or can be a LOT more strict. Like…ride a horse to work strict. They’re not … Continue reading

Posted in Horror Stories | 12 Comments

The Girl Who Met Someone Else

The way to stay out of trouble with serial killers is to avoid being brought to a second location. It’s Serial Killer 101. Let ‘em abduct you, fine, but the real problems start when they toss you in their van. … Continue reading

Posted in Horror Stories | 14 Comments

Interview: A Man Who Stood Up His Date

The following is an email I received from Max D, a loyal reader and Internet dater. Initially, I was very proud… As per your expert instructions I sought out the perfect first date restaurant.  It’s named after an Italian opera, … Continue reading

Posted in Advice, Horror Stories, Your Awful Stories | 60 Comments

The Girl Who Wouldn’t Let Me Leave

When you make a date, I find it’s best to keep it. Rescheduling, even if you have a really good reason, just sends a wave of doubt through an already doubt-riddled experience. “Hey, I’m not feeling well, can we do … Continue reading

Posted in Horror Stories | 3 Comments