Rah-Rah-Ah-Ah-Aha…Roma, Roma-ma…GaGa, ooh-la-la!  Just like GaGa, we wanted your bad romance and you gave it to us. We always knew dating can be scary - but your stories make that claim reach a whole other level. Thank you to everyone who sent in their stories we wish we could give everyone a prize to help heal your dating wounds, but there could only be 1 winner. “Advice From a Jerrk” columnist Jerrod chose his favorite bad romance story (Congratulations to Cara!), and the PLRG team chose some other quality stories to share with you. May they make your Valentine’s Day week seem a little bit brighter…

Winning Entry - “Mr. Most Wanted”

Last year on my birthday, my insane friends treated me to a night on the town. I couldn’t tell you where we went, all I know is that we ended the night at Barleycorn in Wrigley. I ended up meeting some guy and apparently gave him my number. I woke up the next morning on my couch in my dress from the night before with a million texts from this guy (should of been the first red flag). I couldn’t remember his name or what he looked like (the girls told me from what they remembered, he was a good looking guy). I agreed to go out with Mr. Barleycorn and gave him the head’s up that I was a strict vegetarian. A week later I met up with him for our date. He takes me to Shaw’s Crabhouse- where I think the only thing on the menu without meat is a side salad, orders a bottle of wine and begins to tell me about himself….here’s what I learned or what I remembered the most- he was 10 years older than me (really not that big of a deal) and still lived with mom and dad. Dinner continues and so does his drinking. I had a glass of wine and switched to water. He finished the wine and switched to dirty martinis (5 martinis). After dinner he asked if I wanted to head to a bar for another drink- at this point I should of said no, but I didn’t. We go to Harry Caray’s and I continue to drink water. He had 5 more mixed drinks. He started getting all touchy feely with me and when I asked him to stop he wouldn’t. I politely asked him to respect the fact that I said to stop and his reply was “You don’t think I respect women? The last time I had sex was 3 years ago.” At this point it was time to go home. We hop in a cab and he asked the driver to take him to his car so he could drive me home. I told him he would not be driving me anywhere (the cabbie also yelled at him for even thinking to drive at his level of intoxication). I had the cab driver drop me off at the corner, thanked him and started to get out. He then asks if he gets to come with me. I politely say no and he that really pissed hm off. At this point I just say sorry and leave. For the next hour I got texts from him that said things like “well I guess I will just sleep in my car,” “Thanks for nothing bitch,” etc. I ignore the texts and go to bed. Fast forward to Monday, just when we thought it couldn’t get any better, while bored at work I google search Mr. Barleycorn. His name pops up under “Indiana’s Most Wanted.” Intrigued, I click on the site. Up pops his mug shot. Luckily, he was only (I say this lightly) wanted for a re-arrest to failure to appear in court for too many DUI charges….imagine that. So that’s my horrible date. Great story to tell the grandkids.

-Cara

And the runner-ups…

So here I am excited to jump back into the world of dating after my relationship of six years falls apart, and I agree to be set up through a mutual friend to catch a movie with this guy. I’m dressed and ready to go when I get a text message from my date saying he’s running a few minutes late, but when I call him back to clarify how late he informs me that he hasn’t yet left his house (he lives almost an hour away). He suggests that I drive and meet him at the theatre, so I finish getting my things together when I get another text- this time, saying he’s pressed for cash and asking if I would cover him for the movie tonight. Let me be clear, I have no problem paying for a date, but he could not have made a worse first impression! Tardiness, frugality, and the general lack of courtesy to actually call with his little updates were too much for me to handle. This time it was my turn to text back and say something had come up. What a prince charming.

-Anna

My worst was many years back, like 20 year ago, I was 17 and working at the Walgreens on Lawrence and Pulaski in the city. It snowed really bad that day, I mean really bad. I was determined to see my boyfriend and bring him his card that I bought him. So I trudged, yes trudged through snow that was higher than my ankles from Lawrence and Pulaski to Montrose and Kimball. I walked all that way and when I got to his house I found him in nothing but biking shorts and wiping sweat of of his chest and the blonde friend from across the street. He told him they had just been working out. Yeah I bet!

-Candice

My dating disaster starts off as anything but. I met a nice looking gentleman the previous weekend at our local watering hotel. Handsome good looks? Check. Ability to carry on a conversation without putting me to sleep? Check. Left finger sans ring? Check. Lack of obnoxious, rude, drunk friends gallivanting around him? Check and ah how rare! All systems were a go and when he suggested we go to a music/food festival the following weekend I couldn’t help but be excited. The date started off pretty well but I couldn’t help thinking the guy was a bit of a bore. (Was I that hammered when I met him that he seemed funny; and was he that boring sober that he needed to drink in order to have a personality?) When we got to the wine tasting booth he seemed to come out of his shell and really hit it off with the woman pouring the drinks. As we walked back to our high top table nearby he told me that he “sorta used to date” her. Feeling a bit off guard I excused myself to the restroom to redo my pout. When I returned I found the wine girl, my date and lots of laughter at our small high top table. I put on the biggest smile I could muster and said “Hi, I’m Molly,” and extended my hand. She said, “Hi I am Katy, Jason’s girlfriend.” I looked at Jason in utter disbelief and confusion, to which he replied: “Um, we decided to give things another go while you were in the bathroom.” With that, I gracefully walked back to the wine bar and downed a flight of reds

-Molly

If you have relationship or guy-related questions for Jerrod, just send an email to AskJerrod@PoorlittleRichGirls.com. When he’s not working on his advice column, Jerrod is a managing partner of Hub 51, River North’s hottest dining, nightlife and social establishment created by him and his brother, R.J.

Harboring hilarious dating stories?  Dying to dish some dirt or reveal your most embarrassing one-on-one moment? With Valentine’s Day quickly approaching, now’s your chance.

While I typically try to shed light on the way guys think by answering any and all relationship or guy-related questions, it’s only appropriate that I offer an extra installment dedicated to personal accounts of the biggest, boldest (and most horrible) dating moments.  Beginning today, through Friday, February 5th, Chicagoans are encouraged to submit their very best dating story for the chance to win Valentine’s Day dinner for two on February 14th at none other than HUB51.

Hit me with your best encounter at askjerrod@poorlittlerichgirls.com.  What’s there to lose?  You’ll finally get that horrible, hilarious and possibly humiliating story off your chest and perhaps even win a romantic dinner with your sweetheart (or non-sweetheart) on the house, plus a guaranteed reservation for V-Day weekend.  The winner will be announced and the very best stories will be featured online on Monday, February 8th.

(Jerrod Melman)




Jerrod Melman is one of PLRG’s resident contributors who offers his witty wisdom in his bi-weekly column, “Advice from a Jerrk.” If you have relationship or guy-related questions for Jerrod, just send an email to AskJerrod@PoorlittleRichGirls.com. When he’s not working on his advice column, Jerrod is a managing partner of Hub 51, River North’s hottest dining, nightlife and social establishment created by him and his brother, R.J.

Originally published on February 1, 2010.

I am fascinated by the way men and women relate, and if that doesn’t make me an expert, it may make me a kind of student teacher. Hopefully this column will help share a little of what I’ve learned, and maybe shed some light on the way men think, from one man’s perspective. -JM

Over the summer I started dating this guy while we were both living abroad in Italy. After we spent a wonderful three months together, we returned to the States, but he is currently in school in Texas. We talk on the phone regularly and he has on multiple occasions promised to come visit me. I have taken vacation from work in anticipation, but then he bails last second. He says that he cannot afford the trip, but then spends his weekends snowboarding in Colorado. I want to know whether he will ever come out to visit and whether this relationship will continue.

-Waiting in Westchester, 23

You know the answer, stop wasting your time, effort and vacation. Stop messing with Texas.

In your honest opinion, in the first month of dating what expectations do guys have when a girl spends the night? Are guys 100% assuming spending the night means sex? Or do they only assume it’s a 60% chance? Or less?

-Stats not love

Kind of gives a new meaning to “taking a poll.” I’m not sure “assume” is the right word, I’d say hope is better. Either way I’d worry less about that and more about what you’re comfortable with.

Why do guys at bars talk to girls all night* long and then ask for your number and then never call. Why bother asking for the number if you are never going to call?

-Drunk Dialed, Minus the Dialed

*All night = 4 hours x 2 drinks per hour = 8 Drinks = Drunk Chick/Dude

Let’s be honest, the real question is, why didn’t he text? We all know anyone you meet in a bar wasn’t really going call you anyway. He’ll last minute text you, “you out?” at 11:30 on a Saturday night. Or maybe you’ve gotten this one: “up?” at 1:45AM. That means he’s horny, and dreaming of the drunk girl he talked to all night at some bar.

If you really feel like you’re connecting, get his number and take matters into your own hands.



This is the sixth official installment of Jerrod Melman’s column, “Advice from a Jerrk.” If you have relationship or guy-related questions for Jerrod, just send an email to AskJerrod@PoorlittleRichGirls.com.  When he’s not working on his advice column, Jerrod is a managing partner of Hub 51, River North’s hottest dining, nightlife and social establishment created by him and his brother, R.J.

Originally published January 25, 2010

I am fascinated by the way men and women relate, and if that doesn’t make me an expert, it may make me a kind of student teacher. Hopefully this column will help share a little of what I’ve learned, and maybe shed some light on the way men think, from one man’s perspective. -JM

Why does the word “curvy” have a negative connotation?   I am an attractive girl, who works out regularly, with a very feminine physique.   I am considering online dating and all of my friends tell me I can’t say I’m curvy [when describing myself online].   How else can I express the fact that I was blessed with a woman’s body without using this word?

-Blessed with boobs, 28

Obviously you’re friends are concerned that most men reading your profile will interpret “curvy” as “fat.”   You seem very confident in your body type, so I say go with curvy and let your looks speak for themselves.    Do you really want to date a guy who’s afraid of that word anyway?

I was recently with a man who I thought was an urban legend.  He loves to go down on women.   He went down on me for 45 minutes and gave me 3 orgasms in a row.   All women know that men love blowjobs, but I don’t know if guys realize how much women enjoy oral sex as well.  How can I find another man like this?  Is there a way to tell if a guy is really good before you jump in the sack?

-Looking for a talented tongue

As I have never been with a man before, I’m afraid I don’t know of any ways to tell if a guy is, “really good before jumping in the sack.”   In my experience with women, sexual compatibility starts with kissing.   If the kissing is good everything else usually falls into place.   If it turns out the guy doesn’t like going down on you, there might be a chance you’ve found someone who enjoys men himself and can help you with tips on how to spot a man with talent in the sack.

I recently got out of a long-term relationship.  I am still a physical person who needs affection, and have had “relations” with two different men.  No sex, but a bit more than make-outs. However, both guys have done what I would consider rather weird things.   One guy sucked my toes and the other bit my butt so hard he left a mark. Is being a freak the new “in” thing?   Have I been out of the game that long? Whatever happened to just a simple make out session?

-Don’t suck my toes

I think that hook-ups have a lot to do with luck of the draw.   For every toe sucker and ass biter, there’s a man who will go down on you for 45 minutes and give you three orgasms.  Don’t give up.

It’s me again (of “Don’t suck my toes” fame).   The other night I was at a friend’s apartment that she recently moved into with her guy friend that she’s known since high school.   I think he is very attractive.   One night the three of us were sitting around drinking beers and she brought up the reason she believes it was so hard for me to get out of my previous relationship.    She explained that it is my love of sex that kept me with my ex for so long.   Since then, her studly roomie has been coming onto me hardcore.   Do you think he is attracted to me as a person, or just attracted to me because I love sex?

-Don’t suck my toes…But have sex with me

Don’t forget, the fact that you like sex is part of who you are as a person. Why would it be a bad thing if he likes your sexuality? It’s impossible to know what he’s after without getting to know him. You’ve got nothing to lose.

This is the fifth official installment of Jerrod Melman’s column, “Advice from a Jerrk.” If you have relationship or guy-related questions for Jerrod, just send an email to AskJerrod@PoorlittleRichGirls.com. When he’s not working on his advice column, Jerrod is a managing partner of Hub 51, River North’s hottest dining, nightlife and social establishment created by him and his brother, R.J.

Originally published January 11, 2010

I am fascinated by the way men and women relate, and if that doesn’t make me an expert, it may make me a kind of student teacher. Hopefully this column will help share a little of what I’ve learned, and maybe shed some light on the way men think, from one man’s perspective. - JM

Dear Jerrk,

I have a huge problem. I am only attracted to jerks, and I figured with a name like Jerrk you know a lot about them. All of my relationships are filled with drama and mistrust. For example, my current boyfriend constantly breaks into my email and looks at my texts. If he finds anything he doesn’t like he calls me names and starts a fight. My last boyfriend keyed my car after an argument. For some reason, I have never had a stable romantic relationship, despite the fact that my parents have been married for 30 years and are still madly in love!! What am I doing wrong?!

-Addicted to Drama, 27

The relationship that needs the most work right now is the relationship you have with yourself.  If you’re not in therapy, start immediately. You’re parents being happily married for 30 years is great, but it doesn’t give you a free pass to a good relationship.

I went out with this guy I’ve sort of been seeing last night and he was wearing a pair of Heely’s… (I’m NOT kidding… if you don’t know what they are: http://www.zappos.com/heelys). This is definitely not okay for a grown man, correct? He was also wearing a suit if that helps you with the visual any more…He otherwise is great - successful, ambitious, really fun to be around…what should I do? It was a total turn-off for me.

-What’s the Heely-O?

I went back and forth on this one. Most people I talked to called it a deal breaker, but I kind of like his confidence if that is in fact what we’re dealing with. I figure there’s going to be something you dislike about anyone you date; at least with this guy it’s something funny. I think the sensible thing to do is play this one with baseball rules, three strikes and he’s out. It’s up to you to decide how many strikes he gets for his Heely’s.

I met a guy from an online dating website. I have been honest from the beginning that I am looking for a relationship. We have been dating for almost two months and the holidays are rapidly approaching. We have established that we are only dating each other, but he hasn’t mentioned anything about New Years plans. Should I assume that we are doing something? I don’t want to come off needy, but also don’t want to spend New Year’s alone!

-New Year’s Ball Dropped

Assuming you’re going to be together on New Year’s without having made plans will only leave you disappointed. I don’t think there’s anything needy about asking him what his plans are, just be prepared that they might not include you.

This is the fourth official installment of Jerrod Melman’s column, “Advice from a Jerrk.” If you have relationship or guy-related questions for Jerrod, just send an email to AskJerrod@PoorlittleRichGirls.com. When he’s not working on his advice column, Jerrod is a managing partner of Hub 51, River North’s hottest dining, nightlife and social establishment created by him and his brother, R.J.

I am fascinated by the way men and women relate, and if that doesn’t make me an expert, it may make me a kind of student teacher. Hopefully this column will help share a little of what I’ve learned, and maybe shed some light on the way men think, from one man’s perspective. - JM

So…I met a guy three and a half months ago that lives in San Francisco. We hit it off and got along swimmingly! We stayed in touch, from time to time, mostly via text. When we’d text, it would be fun and flirty… but all very light-hearted. I saw him a second time about a month ago. We hung out and it felt like we had known each other for a while. It was great! Since then, however, I’ve only heard from him ONCE - via text - over the course of that entire month. It was fully unprompted: he texted me. (Side note: I took his number out of my phone so as to avoid any unnecessary drunk dialing/texting.) While I wanted to prove a point and not respond at all, the majority of my girlfriends urged me to text back. So, I waited over a day to respond and ended up writing something cute but also very neutral. And he hasn’t responded! Why would a guy text me, out of the blue, and then not respond?

-Troubled Texter

Let’s clarify quickly - “it was great” means “we hooked up”. And that is great, but the important detail is this guy lives in San Francisco and you don’t. I’m not saying it’s impossible that a guy in a similar situation would want more in terms of a relationship, but in this given situation I don’t think he does. My guess would be it’s exciting for him to get to know you, and he enjoys the idea of having a random hookup every now and again when you or he visit each other’s city. You said it yourself; it’s been mostly “fun and flirty.” If that’s something you think you can enjoy then keep going. But if you’re looking for the time, attention and text response time of a boyfriend, I think you need to look elsewhere.

Am I portraying myself in a bad light if a guy asks me to dinner and I tell him I’d prefer drinks? It isn’t that I don’t want to spend time with the guy - but dinners can be long and slow, and sometimes (or most of the time!) I’d rather just get tipsy at a nice bar! Do you think if I want a guy to take me seriously I’d better put on a happy face and sit through dinner with him?

-Wine me but don’t dine me

If that’s honestly what you prefer, then any guy put off by that probably wasn’t for you in the first place. I don’t think there’s anything wrong with keeping your initial time commitment brief until you get to know a guy. Why not say something like, “I don’t have time for a full dinner, but I’d love to grab a drink.” If it’s going terribly you can always say you have to go do whatever it is you said you had to do. If it’s going well I’m sure you’ll figure it out from there.

What is the key to a successful marriage?

-Kristin, 26

Separate bathrooms.

This is the third official installment of Jerrod Melman’s column, “Advice from a Jerrk.” If you have relationship or guy-related questions for Jerrod, just send an email to AskJerrod@PoorlittleRichGirls.com. When he’s not working on his advice column, Jerrod is a managing partner of Hub 51, River North’s hottest dining, nightlife and social establishment created by him and his brother, R.J.

I am fascinated by the way men and women relate, and if that doesn’t make me an expert, it may make me a kind of student teacher. Hopefully this column will help share a little of what I’ve learned, and maybe shed some light on the way men think, from one man’s perspective. - JM

I have a best friend who is a guy and I think I am starting to develop feelings for him. From the start our conversations have been very flirty, but how can I know if he feels the same way? We have just recently become friends (we are working on a charity project together) so I don’t think we have moved into that “friend zone” just yet. Should I tell him how I feel, or just let it slip into the friend zone?

- Elisa, 24

I think the “friend” zone only applies to guys, so I wouldn’t worry about that. That being said, the “girls that rush into telling guys how they feel” zone is very real. I think you should relax and enjoy your time with this guy and give him a chance to make a move. Guys like a bit of a chase. I’m not saying play games, I’m saying continue to be flirty and show interest and see if he asks you out. If he’s worth dating, he’ll man up.

I’ve been dating my boyfriend for over a year. Consequently, I’ve become very good friends with his friends. He graduated already and some of his friends are younger (like me) and are still around on campus. But whenever I hang out with his friends he freaks out. I think he should be happy that I get along with his friends so well, but instead he just gets angry when we hang out. His friends have legitimately become my friends over the last year and I don’t understand why he can’t be happy about this. Being friends with his friends, good thing or bad thing?

- Confused co-ed, 21

This is a tricky question with a lot of variables. If I just started dating someone and she tried to make my friends her friends too quickly, I’m sure I would be annoyed. Most likely after a year of dating that would be less of an issue. The real question is not whether it’s good or bad that you’re friends with his friends. It’s why does he freak when you hang out with them? I think the best thing you can do is to ask him. Maybe he thinks one of his guy friends likes you and he is insecure about that. Maybe he had a bad experience in the past with a girlfriend cheating on him. Maybe he knows you won’t be together much longer and doesn’t like the idea of you having the same group of friends. Often times when guys are up to something behind your back they become less trusting of you, so it’s even a possibility that he’s doing something you wouldn’t like and doesn’t want his friends to spill the beans. Bottom line, you won’t know unless you ask (in a calm and sober manner that won’t put him on the defensive). Before you do, you might want to think how you would feel if the situation were reversed.

I’m wondering if you can finally put to rest the question of when to have sex with the guy you’re dating. Should women listen to the new-age-turned-old-school therapists who insist they should wait 3 months before sleeping with the man they’re dating? Do men really lose respect for women if they want to have sex “too early”?

Resexfully yours,
Jessica

The answer to this question, like most questions is: it depends. Great meals usually don’t start with dessert. That being said, sometimes you just want to indulge your sweet tooth. There’s nothing wrong with sleeping with a guy early on, you just have to understand it changes the meaning of sex in the relationship. Having sex right out of the gate inherently causes sex to lose some of its value. On the flip side, waiting too long or creating a rigid timeline can cause you to lose spontaneity. Rather than worrying about losing a guy’s respect, I think women would be better served evaluating how they feel and proceeding accordingly. I’m sure there will be some guys you just want to sleep with and others you will want to get to know, trust and develop a relationship with before having sex. Either way, the goal is not making sex about what you think a guy wants from you, but rather an indication of how you feel about him, keeping in mind the better you know someone and the more you trust and care about someone, the better the sex will be.

What’s your way of showing a girl you are interested or care about her?

This is the second official installment of Jerrod Melman’s column, “Advice from a Jerrk.” If you have relationship or guy-related questions for Jerrod, just send an email to AskJerrod@PoorlittleRichGirls.com. When he’s not working on his advice column, Jerrod is a managing partner of Hub 51, River North’s hottest dining, nightlife and social establishment created by him and his brother, R.J.

Next week we’ll be running the first official installment of Jerrod Melman’s column, “Advice from a Jerrk.” If you have relationship or guy-related questions for Jerrod, just send him an email at AskJerrod@PoorlittleRichGirls.com. When he’s not working on his advice column, Jerrod is a managing partner of Hub 51, River North’s hottest dining, nightlife and social establishment created by him and his brother, R.J. But, first, we’ll allow him to introduce himself…

I am not a relationship expert. At the rate I’m going, I will probably never be. I didn’t go to graduate school and get a PhD in this subject. Even if there was such a thing, I wasn’t that good at school. On paper I am in no way qualified for this job. I’ve been on great dates and terrible dates and everything in between. I’ve dumped girls and been dumped, I’ve blown girls off and been blown off, dented hearts and had mine dented. I’ve done and said things that made girls cry, then done and said things I didn’t necessarily mean to make them stop. I’m not always proud of these things, and I’m certainly not trying to brag, but in my few years as a dating adult, I think I’ve learned a lot.

C'mon, does this guy look like a jerk to you!?

I admit that I am fascinated by the way men and women relate, and if that doesn’t make me an expert, it may make me a kind of student teacher. Hopefully this column will help share a little of what I’ve learned, and maybe shed some light on the way men think, from one man’s perspective. The PLRGs and I wanted to call the column “Advice from a Jerrk”, hopefully not because I’m a jerk (I do have my moments,) but because my advice tends to be blunt and non-sugar coated. That being said, I’m here to try to help guide my readers through the dating maze. I confess I’m both nervous and excited, and I commit that I will do the best I can to call your situation like I see it. Ask me anything you want, just email me at AskJerrod@PoorLittleRichGirls.com. I’ll give you my best most honest answer, and hopefully it won’t make you cry.

(Jerrod Melman)