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Having recently begun dating again, I am reminded of just how much dating can suck. This is a place for my own stories and musings on the chaos of singledom, as well as a place for you to share and submit your own dating stories.

As calloused as we may be, we realize dating can also be a positive experience and even fun. We’d love to hear those stories as well! Inspire us!

To submit your own story to “Dating Can Suck” please click the “Story Submission” link at the top or to the right.

Feel free to peruse the dating stories below.

Scarred For Life

I met this guy online and chatted with him over the next two weeks. He seemed nice enough, so I invited him to come to a party with me. He did live two hours away, but he seemed quite fine with driving to see me. I saw a picture of him that looked okay. As I waited outside for him, I saw this short, long-haired guy with leather pants. Then the worst came. I saw his face, and yikes! He had the worst case of bug eyes I’ve ever seen! They literally looked like they were about to pop out of his head. And his jaw was all uneven. Feeling responsible for getting myself into this situation, we continued to the party. Well, not only was he hideous, but he would not stop trying to grope me below the belt in front of everyone. So, I got hammered that night and did have sex with him. Afterwards, he told me he loved me. This freaked me out! I hardly knew him. Plus, he was gross-looking and way annoying. I was still intoxicated and at the party, but I needed out. I told him I had to grab some CDs from my car, and I sped off. That whole night he called me approximately fifty-seven times and left twenty-three voicemails. Finally, I called him back but just to tell him I didn’t appreciate him giving me a phony picture and to tell him that he was the ugliest, most annoying person I’d ever met, that I never wanted to talk to him again, and then I hung up. He still called. So, I had to block his number and change my username. This one was whacked! I’m still scarred for life that I even kissed him! — Cassandra, 26

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March 27th, 2007 by: Steve

Guys: 10 first-date fumbles

Just to be fair to both genders :)

By Lori Gottlieb

1. Going on a rant about a former significant other.

No good can come from talking about an ex-girlfriend on a first date. Saying something positive about an ex is threatening, and saying something negative is just plain annoying. My friend Leslie agrees: “My favorite annoying first date is the guy who spent the entire time describing in detail how nasty his ex was,” she said. “By the end of the date, he had pointed out the restaurant where she threw a drink at him and the street corner where she screamed at him about his lack of sexual prowess.” The first date is about the two of you getting to know each other. Bringing the ex into the conversation makes it seem like three’s a crowd.

2. Divulging too much personal information that’s not flattering.

Take a hint from comedian Chris Rock, whose dating advice goes something like this: When you first meet someone, you’re not you. You’re the ambassador of you. In other words, this is not the time for full disclosure. I went on a first date with a guy who told me that he takes antidepressants, that he tends to be a slob, and that his family doesn’t get along. “I’d really like to see you again,” he said, “but I think I should be upfront about who I am from the beginning.” Even worse are guys who reveal unflattering personal information without even realizing that the information isn’t flattering. “My dog is my life,” a guy told my friend Sherene on their first date. “I’ve had the dog since I was a kid,” he added shamelessly. “I live with my parents.” The information was bad, but the fact that he had no idea it was bad made it horrifying. Remember: This is a date, not a therapy session.

3. Making the date feel like a job interview.

Let’s face it: A first date is a job interview (for the position of significant other). But if a woman is going to put on a cute outfit and blow-dry her hair for you, try not to make her feel like she’s in the room with the head of human resources. She’d rather have a casual conversation than be subjected to obvious probes like, “How long has it been since your last relationship?” Just as bad are guys who try to suss out key information by dropping calculating questions into the conversation. My friend Sara found it particularly irritating when a guy tried to figure out her age by asking her opinion of the 1972 Olympics and then saying, “Oh, but you couldn’t possibly remember that” in a questioning tone.

4. Having too much attitude.

Laurie, a single woman in New York, was asked on a first date what TV shows she watches. When her date learned that she didn’t like the show Seinfeld, he didn’t believe her. Then he wouldn’t let it go for the entire meal. “He just couldn’t fathom my not liking that show,” Laurie explained. “It was as if I’d just said, “Yes, I live my life without consuming any liquids.”“ Guys, if you want a second dinner, don’t spend the first one trying to convince your date that she’s not normal.

5. Admiring other women.

Most guys know better than to stare at other women while on a first date. But it’s just as exasperating if your date asks you what you thought of the latest blockbuster hit, and your response is to go on a tear about how beautiful Angelina Jolie’s lips are. If you think the woman sitting across from you is ever going to be secure enough to kiss you after that, think again.

6. Complaining about the venue.

Don’t ask your date to “pick any place you want to go,” only to whine about it once you’re there. That happened to Liz, who chose a place with a lunchtime tasting menu. Not only did the guy grumble, but “he proceeded to tell me that he had had a big breakfast and wondered who could eat a three-course lunch,” she said. “I told him, “I could” and pointed to myself and then to every other diner in the restaurant.”

7. Arguing with your date.

It’s one thing to talk about current events if there’s a lull in the conversation. But it’s quite another to ask your date’s opinion on anything from the Middle East to the election and then get into an argument with her, no matter what she says. That happened to 29-year-old Melissa when she and her date got into it about public versus private schools. “I was annoyed that he fought me on so many things” especially on our first date,” she said.

8. Eating your date’s dessert.

Unless you’re at a Chinese restaurant, there’s a reason you each have your own plate. Just because a woman might eat more slowly doesn’t give you license to take a bite of a virtual stranger’s meal. Or, in Liz’s case, her date didn’t even wait until she’d taken a bite herself. “When my dessert arrived,” she said, “my date reached across the table and, with his fork, speared my gateau au chocolate. Talk about annoying.”

9. Not walking her to safety at the end of the date.

Almost as off-putting as the overzealous guy who goes in for a kiss too aggressively is the guy who leaves his date standing there on the street at night instead of walking her to the safety of her car or a cab. This irked my pal Julia. “True, we were going in two different directions” but hello? “Take care of the girl first!” she said. “Stuff like that usually points to bigger problems!”

10. Saying, “I’ll be in touch” after the date goes badly.

Your date knows that the evening went badly, and you know she knows it, so why say that you’ll call when it’s obvious you won’t” “I’d like him to say, “Good to meet you, take care,”“ said Monica, who feels that you can still be nice without being annoying (or making a woman sit by the phone).

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March 20th, 2007 by: Steve

Ladies: Worst first-date moves

This was sent to me by a reader and I thought I would share it with you.

By Dan Bova

1. Blabbing about your ex

He would never order the steak rare like you just did! OK. He would never think of driving a car like the one you do! Great. He would never wear a jacket like yours! Fascinating. Listen, we guys want to go out to dinner to get know you better, not the loser you broke up with two months ago. The more you talk about him, the more we’ll think that we’ve got “rebound” stamped on our collective forehead. And here’s a weird little guy trait you might not know: Trash the dude too much, and we might start to mentally take his side. Nobody could be that bad, we’ll think. You’re just being too critical, we’ll think. And worse, we’ll wonder if are you going to be this harsh on us! Because if so, what the heck are we doing splitting dessert with you? Why aren’t we out having fun like that dude who escaped before you henpecked him to death?

2. Asking too many finance-based questions about your date’s job

It’s one thing to take an interest in what we do, but save the “Does your company give you stock options?” Questions for a little further down the road. Like after you get engaged.

3. Not eating anything

My buddy Colin put it best when he said, “I have no desire to date Gandhi.” Going on a one-night-only hunger strike is just silly. It makes us feel like slobs when we’re plowing through a steak and you’re picking through a mixed green salad with the dressing on the side. Plus, they say that if you want to know how a person will be in bed, watch the way she eats. If you show no signs of enjoying sinful indulgences at the dinner table, it doesn’t exactly get a guy’s heart racing to imagine what’s to come a few dates from now.

4. Picking really expensive restaurants

On a birthday, sure, we’re totally up for blowing a paycheck on dinner. But on the first date? Not so much. Using men to take an unpaid tour of the Zagat’s guide is right up there with “running over my dog” as one of the suckiest first date misdeeds a woman can commit.

5. Acting like we’re boyfriend and girlfriend too fast

Guys get just as excited as you when they meet someone cool and fun who doesn’t appear to have any weird quirks like, say, being on the run from the law. But definitely leave him wanting more. Get too clingy too fast, and you’ll scare him off in a hurry. Nothing screams “psycho girlfriend” like giving him a cutesy nickname 15 minutes into your first date.

6. Whining about how hard it is to meet people these days

“When a girl is going on and on about how hard it is “out there” in the dating world, I can’t help but think, what’s wrong with this person that no one wants to be with her?” says my cousin James. Plus, it doesn’t exactly make a guy feel special if he knows he’s number 11 in the line of guys you dated that month.

7. Using us like a therapist

One of the great things about being in a long-term relationship is having someone to talk to when you’re down, a shoulder to lean on when you’re stressed out of your mind. But save discussions of unresolved issues with your mother for a little further along than minute 12 of your first dinner date. You want to leave him thinking, “Man, that girl was a blast!” And not, “Man, that girl was a drag!” First dates are all about having fun, right?

8. Acting flirty with other guys at the bar or, worse, with our friends

As I said, first dates are all about having fun, But not too much fun. There’s a fine line between being outgoing and being on the prowl for anything that moves.

9. Not having an opinion

Would you like to go see a movie or go for drinks? It’s up to you. Do you like Italian food? Whatever you want to eat. One of the major goals of a first date is to find out if two people are compatible. We want to find out what you like, what you think. So drop the overly polite act, and give us a peek into what’s going on in your brain. Now we’re not asking you to turn into Bill O’Reilly, but please, give us an opinion! How can we enjoy our rigatoni special if we’re afraid that you actually hate garlic and are allergic to red wine?

10. Acting too motherly

Oedipus dated his mother, and we all know how that turned out. Never mind the first date, keep the “You need a haircut” and “Button up your jacket” comments in check for the first year!

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March 19th, 2007 by: Steve

Dating, Dining, and…. Dentures??

Another great dating tale.

After three years of dating and twenty years of marriage to the same girl we divorced, and uncomfortably I got back into the dating scene after all that time. I hated the bar scene, so I chose a newspaper dating service. The first exchange with these potential dates was by letter. One woman, who admitted in her letter to me to be only 4 years older than my 38 years, sent me a picture. I noticed in the picture that her hairstyle was a little out of date. But, we arranged by phone to meet in a local restaurant anyway for our date. On the night we were to meet, I looked for her in the restaurant, but couldn’t find her. Even though I saw a woman that was wearing the outfit she said she’d be wearing, the woman didn’t look like the picture. After several minutes of wondering if I had been stood up, I wandered into the bar of the restaurant and grabbed a stool. The woman in the restaurant wearing the clothes as described in our phone call walked up to me and introduced herself! It was my blind date - at about age 60 (and an OLD 60 at that)! The picture she had mailed me, as she explained, was a High School picture of her from the 1950’s! I felt obligated to continue the date anyway, even though it felt like I was out with my mother. Everyone in the restaurant was staring at us. This woman had loose dentures that whistled when she talked and her wig was on sideways! She even insisted on holding my hand! Later, after dinner, she actually wanted to go parking, but I told her I felt sick (which I did after that suggestion) and needed to go home. I promised to call her the next day, which I did. I told her on the phone that I was sorry, but I didn’t appreciate her lying about her age by at least 20 years! She actually got angry at me and hung up on me and then would call for weeks after that and not say a word, but just slam the phone down in my ear. — David, 46

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March 18th, 2007 by: Steve

A little advice..

..is in order i think. Now this goes for both men and women. “Date at your own level!”. I have heard this before although i don’t recall where. Let me explain. Ladies, if you are a lets say a seven (7) on a scale of one to ten, then be more than willing to date men who are within a seven’s (7) level. You are not held to only sevens (7) in your level. You may also go two steps higher or lower. So you could date a five (5) and be OK or you can date an eight (8) and feel like you won the lottery. Men the same for you. If you are a five (5) and get a seven, don’t blow it. If you get a three (3) be nice to her. She just may be the best thing that has happened to you. Now, here is the great thing about dating on your level. MATH!!!. It works like this, and this is for both men and women. You can have multiple partners as long as the total score for all partners is within your level. So a seven (7) could have a nine (9) OR a five (5) and a four (4) OR two fours (4) and a one (1). You could even have nine ones (1) if you wanted but I assume no liability with that one. So it is simple folks date within your level and be creative in your math.

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March 15th, 2007 by: Steve

You Dirty Rat!!!!

We have all been dumped at one time or another. It can really suck. So what do we do to get through it??? Well my friends that is the question. A friend of mine recently shared with me one of her favorite break up songs so I am sharing it with you. What do you do?

You Dirty Rat

You never write, you never call
You just stand around and smile so happily
The government could never do
As worse a things as you have done to me

Well I should cry, but I’ve done too much already
I can’t lie, cuz you’re better at that than I’ll every be
And it won’t take us back to you and me
Being all in love
You call me names, and you’re never home
And all I got ta show is a kissin jones
You talk too much, but not to me
Cuz too much of this love I’ll never see

Well I should cry, but I’ve done too much already
I can’t lie, cuz you’re better at that than I’ll every be
And it won’t take us back to you and me
Being all in love

You dirty rat, you broke my heart
I can’t believe it went this far
Turn out the heat, blow out the spark
Oh…
Now I gotta say before it all gets said
I look alive but I feel dead
And as for us are we still good friends?
Oh, no, no…

Well I should cry, but I’ve done too much already
I can’t lie, cuz you’re better at that than I’ll every be
And it won’t take us back to you and me
Being all in love

You dirty rat, and I gotta say
You sure know how to wreck my day
Turn off the sun and walk away
Oh…
But now I just what to find
And who is who this next in line
And as for us, is there still time?
Oh, no, no, no…

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March 13th, 2007 by: Steve

Booger Hand!

From Netscape…too funny to pass up

I had been dating this guy for about 2 months. I decided to stop in at a bookstore because we had a few moments to spare before the start of the movie we were going to see. After showing me a really romantic picture from a book he was looking at, he leaned toward me and, in a really sexy voice, asked if he could kiss me. Just when I was getting ready to pucker up, I saw the biggest booger hanging off his mustache. I was so disgusted that I refused to kiss him, and told him why. So he wiped it off his mouth and onto his pants, and then tried to caress my face with the same booger hand! He ended up seeing the movie by himself. — Lily, 24

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March 8th, 2007 by: Steve

Ladies, Stop It!!!!!!!

What is it with some women? They think its OK to play dudes. OK OK, I know it goes the other way too. But since I am a guy i am not in the habit of playing guys. I am tired of being played. It seems that women (not all, I am not that stupid) have no problem playing guys. They tell you what they think you want to hear, lead them on, make them believe there is something there when they have not sincere intentions whatsoever. And just when the guy thinks all is well, BAM!, “its over”, “talk to the hand”. Well stop it ladies. While it is true that most guys are not as sensitive and feeling as women, some are. I have talked to a few guys over the last few days who have just been destroyed by lying conniving women. Whatever happened to genuineness and sincerity and honesty and integrity? Maybe some people need to relearn the golden rule.

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March 6th, 2007 by: Steve

Long Ass Night

I have been holding on to this story for a while now trying to decide if I should post it. Guess what I decided. :)

I have been talking to this lady, I’ll call her “K”, for a few months now. Not everyday mind you but every couple of weeks we would talk. We often said that we should meet and chat and have dinner or something. Well i did not really put a lot of thought into this because it seemed that it would NEVER happen. She just seemed to distracted. In fact there were times that we would be talking and she would have to go and would say “I’ll call you right back”. I’m like “OK, cool”. She would never call back. So I really did not think we would ever meet.

Well one Friday we were talking and decided that we should meet that night for dinner. I was like “wow, its really gonna happen”. Anyway I drove down to her house, nearly an hour away. I got there and rang the bell. She answered the door but was on the phone. Anyway I stood in the foyer for nearly 15 minutes while she talked on the phone. She finally ended the call and invited me into the family room to sit down and visit for a bit. After maybe five minutes she got another phone call. So there I sat for maybe another twenty minutes while she talked. She again ended the call apologizing profusely to me. We we started to visit again when she received another phone call. So once again I was sitting listening to her on the phone. Once again she ended the call and apologized. We resumed visiting for just a few minutes when the doorbell rang. She answered it I heard her talking to a man. They soon both appeared in the family room. She introduced me but I don’t remember his name. Anyway he came in and sat down on the couch between my “date” and me. My “date” and he spent the next almost 2 hrs talking business. Apparently they are trying to help each other build their respective businesses. They talked about clients and successes and failures.. I was just wanting dinner. I should tell you that I was starving (I had not eaten since 11:30 am and it was now after 6 pm. So yeah I was hungry). My “dates’” friend even put in a video that they started to watch. They discussed some movie called “The Secret”. At the time I was completely unfamiliar with this movie. I have since learned a bit about it. Anyway I was feeling very uncomfortable being an onlooker and a kind of eavesdropper. It was after 10 pm when they ended their conversation and he left. Now i had said maybe two words in the last 2 hrs. OK I was really struggling at this point. I had a headache and I needed to eat. Finally he left. We had just started talking again when she received yet another phone call. This time however she told the caller that she could not talk and promptly hung up. That was nice of her. For the next hour to hour and a half I listened to her talk about her ex husband and what a loser he was. I tried to be understanding and attentive but found myself getting more uncomfortable. My body was literally shutting down. I did not know how to get out of there without being rude. I think I might have even had a bit of a panic attack. Finally at 12:20, she stopped talking and I said “I should go”. I have never been so relieved to end a date. I only went down there for dinner and NEVER even got to eat. DAMN.

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March 5th, 2007 by: Steve

Are you having fun?? Yeah…well no.

OK this is just too good to not post. I had been talking to this very nice lady online and over IM and on the phone for a week or more. We decided that we should go out. I told her that there was a dinner at the Hard Rock Cafe and at a local theater afterwards on Friday night (an activity with other singles in the area) and would she like to go. She said she would love to. So I picked up my date at the established time and headed to the restaurant. We got there and were greeted by the ‘hostess’ of the party. The ‘hostess’ informed us that she had planned some ‘get to know each other’ activities and gave us instructions. Anyway, we both started participating in the activities. Now it turned out to be a fairly large group, maybe 50+ which is a lot of people. I thought it was great that my date was participating and she seemed to be having a good time. After a few minutes of the activity we sat ourselves at a table and proceeded to talk and visit. I was very attentive to her as this was her first “single activity”. Well we ordered dinner and visited some more. I introduced her to numerous other single people from the party. I thought everything was going fine and she was enjoying herself. Well when she finished her dinner she asked if she could borrow my cell phone, to which i replied “absolutely”. She walked to a quieter area of the restaurant to make a call. Now I am thinking she is checking on her kids, so when she returns I ask “is everything ok?”. She replied “yes…well actually I just called a friend to come and get me”. I could not believe it. WTH??? She said that there were too many people and it was too much for her. Well i was kinda shocked. I really did not know what to say so i just said “OK”. I have NEVER had a date leave in the MIDDLE of a date before. So this was a first for me. Ten minutes later she was gone. Now there is one for the books. LOL. Yeah, dating can suck :)

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March 5th, 2007 by: Steve

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