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Dating Tips from Yours Truly….for MEN!


I am about to let you all in on a little secret. Throughout my life, I have been good at three things…The board game Clue, making the best mac and cheese you will ever taste, and helping my guy friends find women. Yes, I am an awesome wingman…uh, I mean, wingwoman.

I am about to divulge my secrets I’ve learned both from experience and passed down to me by my mother, who was quite the sausage magnet in her day. She inherited this trait from her mother, who got it from her mother and so on and so forth.

I would like to start with the age-old question… “Why do all the best looking guys tend to like bitches?” This is a question I used to ask myself until a couple years ago. I was walking around Union Square and outside of an NYU building I saw this amazingly attractive man. Attached to his face was the cliché boobylicious slut; you know the type: bleached blonde hair, over-inflated breasts, fake tan, and enormous sunglasses. I watched as he slapped her on the ass and she walked off to shop at Deisel. I was so disgusted by the display that I approached him on the subject. He was, of course, as superficial as I had expected. An enormous ex-fraternity jock who was in actuality way past his prime with wrinkles forming around his eyes and jaw. My intention was not to date him; I simply wanted to know what he saw in a woman like her. He proceeded to lean into me, his gassy breath smelling like beer, and told me that he would be happy to take me to dinner and explain in more detail. I laughed in his face and walked off. A few minutes later, this average looking guy walked up to me in a determined manner. He said, “Hey, I saw you talking to Dave. He and I go way back,” he paused and rolled his eyes, “What do girls see in guys like him?” I immediately replied. “I am trying to figure out the opposite: why great guys are always are going after sluts.” He started to laugh and then said… “I think the real question is why are all the great women going for assholes?” He then asked me out.

We decided to go see a movie. When I walked up to the front of the movie theater, he had morphed out of his sweatshirt and tennis shoes into this amazing black ensemble with fitted pants (but not too fitted), a button down shirt, and a black belt with a simple matte silver buckle. I’m not talking some hand-me-down outfit from his older brother…he looked incredible. And I was the unassuming bitch who didn’t see it.

So the first step to getting a girlfriend…Close your eyes and listen to your brain. Beauty is deceiving. From afar, the jock looked hot, but up close, he was tired and leather-like. Whereas the second man was incredibly attractive and I hadn’t noticed because I gravitated toward what society’s standard of “hot” is. If you feel a connection, go for it. Listen to your heart, brain, loins…pretty much everything except your eyes.

It’s as easy as ‘hi.’ I am told a lot of the time that I am a kiss ass. This is because when I see something good in someone, I say it. It is my personal theory that you should ask out as many girls as you can. If you see a girl walk by whom you are attracted to, say hello. See how she reacts and if she is open and receptive, keep the conversation going with statements and questions that she can’t just answer “yes” and “no” to. The worst thing that could happen… she spits on you and tells you she would rather drink a glass of her own bile than go on a date. If she says this, then she is a heartless bitch who doesn’t deserve you. On the other hand, she could say yes. All because you had the balls to say what most men find to be the scariest word in the English vocabulary: Hi.

Go beyond the bar. A bar may just be the worst place to meet a woman. Girls at bars are skeptical of every man who talks to them. Even the sweetest woman will turn into a raging biyotch if she suspects your intentions are to only get in her pants. Furthermore, she will most likely have a posse of friends surrounding her whose defenses are all up. Get passed this idea and strike up a conversation with a woman at the gym. Or at your local coffee shop. Or at an indie movie house. Most likely she will be more willing to engage in conversation, and you’ll already know that you have something in common.

Date for fun. If it isn’t fun, get the hell out of the relationship. You’re dating; this isn’t life or death, so why make it out to be anything more than what it is. They say that children playing house begin to learn what real life relationships are, and how they work. I agree. Children learn by play. If it works so well why did we, adults, stop playing? So go out and play house. Have fun and learn about the opposite sex.

Shoot from the hip. On a first date do something outlandish and daring. Randomness is an easy way to break habit, and women usually love to be surprised. Take her to play paint ball…it will remind her of a scene from 10 Things I Hate About You. Do you golf? Bring her to the driving range and give her some pointers. Is she new to the city? Go on a walking tour or bring her to a few of your favorite spots. Be memorable. Even if this particular relationship doesn’t work out, you want to be remembered as the guy who set the standards for all other dates.

Think outside of the bouquet. What do you think to bring on a date? Flowers? Chocolates? Jewelry? These are all nice—women love to receive gifts (though let me state the obvious here…stay away from jewelry during the early dates. WAY too intense). Does she have a dog? Bring her dog a toy or treat. Did she just finish writing her thesis? Bring her a celebratory cupcake. Does she love to read? Bring a copy of your favorite book for her to borrow. If you two have an inside joke, use it to inspire a small gift. Flowers are classic, so if you go this route, make sure that you find out her favorite kind prior to the date. Do so candidly and she’ll be quite impressed. And make sure if you buy a bouquet of flowers for your date to buy a single flower for each of the girls that she lives with. This makes the statement that you care about the people around her. Dogging her roommates is the easiest way to ruin a relationship. However, this must be executed with caution. Roommates will see right though a con artist.

Never buy flowers to say I’m sorry. Why do men buy women flowers as a general? Here is my theory: In caveman days, hunters would go out looking for food. They would spend all day searching with a group of men for mammoths and saber-tooth tigers, while back at the cave the women would look after the cave babies and launder the loincloths. On the bad days, when the cavemen could find no food, they knew they couldn’t return to their homes empty-handed, so they’d pick wildflowers and bring them back to show their wives. The cavemen would tell them that they were so distracted by the beauty of the flowers that after seeing them, they immediately thought of their wives and could no longer concentrate on hunting. The wives, very grateful that their husbands compared their beauty to the beauty of the flowers, would sigh, consumed with love.

Now, of course all this caveman stuff is bullshit. But my point is still valid: don’t exploit the power of the flower by using it to say I’m sorry. Flowers are a symbol of beauty whereas chocolates are a symbol of “sorry I fucked up.” It says, “Look, I am sorry I messed up. Here, get fat, and I’ll prove how much I love you by sexing up your bloated ass anyway tonight.” But seriously, if you do make a mistake, be sure to include a sincere apology with those chocolates. She will probably be crying… so bring Kleenex to show that you anticipate her needs. Look into her red, swollen eyes and tell her how sorry you are, followed immediately by “tell me what I can do to fix this.” Now it is up to her. She will tell you what you can do… and then do it. I know what your thinking ,”what if she says, ‘go cut off your wank, you pathetic, lying bastard!’?” Have no fear…this won’t happen. She wants your penis intact just as much as you do. And for those of you who really messed up… If she does tell you to cut off your dick, then you are way past the apologetic phase…. Learn from you mistakes and get the hell out of there before she turns Lorena Bobbit on you.

Words can be stronger than Actions. Sometimes. You don’t always have to climb Mount Everest for a girl to make us feel special. Girls like to be complimented. We like it when you tell us we are beautiful. We like it when you respect our brain. We want to feel cherished and it is your job to make us feel so. A pick up line is simply an honest statement that some pig exploited and destroyed. If a girl is attracted to you, she will consider your “line” to be charming. If she’s not into you—regardless of what you say—she can and probably will make it known that you were just using a line. So go ahead and use them. It’s a risk, but at the end of the day, even if we’re not into the guy who hit on us, we’re happy he did so because it is a compliment.

Your girlfriend will look like her mother in twenty years. Assuming you make it to this point in the relationship, be sure to talk to her parents as if you were talking to her. Chances are, she’s already told them a lot about you, so act like yourself. They’ll see through any show you put on. First, you are a young man. Her dad was one once, and her mom dated them at one point in time. They know what you two are up to.

Don’t trash talk them. Even if they could have been the best friends of Mr. and Mrs. Hitler, they are the reason you are getting to go out with this girl. They made her, and for that one reason they deserve your respect.

So there, those are my pearls of wisdom. Take these gems and go get yourself girlfriend. But before you go seeking out strangers, I’d like to add this sidebar: don’t overlook what’s right under your nose. Sometimes the greatest of girls are the ones you talk to everyday. If you didn’t enjoy their company you wouldn’t spend all the time you do hanging out with them. There is the possibility of losing the friendship…but there is always that chance when your heart is involved. That’s the beauty of love; the fact that you can tell that person, “I know my heart could get shattered into a million pieces, but you’re worth the risk.” And believe me—it is worth the risk.

4 Responses to “Dating Tips from Yours Truly….for MEN!”

  1. Merry Monteleone Says:

    Wow, well there’s an interesting thread…. okay, I’m going to jump in here because I’m older and wiser, well, maybe not wiser, but here goes:

    There is a reason the hot guy always goes out with the bitch, it’s a challenge… seriously, it is - it’s quaint and stupid and needy, and yet it’s true. They (all men, regardless of hotness… all women, too, for that matter) lose interest really fast if it’s easy.

    When I was in my early twenties one of my guy friends used to joke about me having a ‘harem’ because I usually had a handful a guys with me at any given time. I was not gorgeous, I was cute and I had a good body but I was not what I would consider a ‘hottie’. I knew a lot of girls that were far more attractive than me, and they didn’t get as much male attention or the same type of male attention. Why?

    Well, I had a few female acquaintances who thought I must be easy (jealous much?) Here’s what I can share, sleeping around will actually have the opposite effect, I’ve seen it happen. Hey, if you want to, it’s your life, but if you’ll jump and go to some guy’s house in the middle of the night with no strings attached, he’s not going to treat you like gold because you’re not demanding it. I had that much male attention because I was quite bitchy. Still am, but that’s another story… and I don’t mean needlessly cruel, I just mean I wouldn’t blush and be all infatuated because some cute/rich/whatever guy asked me out or paid attention to me. Generally, the guys I dated were not the most handsome or financially secure (most of them were broke and average… except the one who looked like Brad Pitt, kid you not and I broke up with him - why? because he opened his mouth and ruined the whole effect).

    Those old rules about dating - play hard to get, why buy the cow… yada, yada… those all still work. The thing is, they’re all games. They’ll get you a boyfriend and get you a date, but if you want an actual relationship, you’re going to have to open up and take the chance on getting crushed - or stay closed and miss out… just like dieting and exercise, there’s really no shortcut. We all have to pay the dues to get the prize.

  2. Ello Says:

    Oh Colleen! You need to write for a magazine! This was great!

    I totally agree with you about the bar thing. No boyfriend comes out of a bar. Usually it’s only sex! I’m all for dating friends of friends. That’s really where the best way to meet people are and the more friends you make the more friends of friends you can meet.

    And I love Merry’s approach also!

    My tip is one most girls will never follow. But I believe is being yourself. Completely. My husband can never complain that I fooled him into thinking he was getting anything but who I am.

  3. Jerseygirl89 Says:

    This is my favorite dating advice:
    “Don’t play hard to get. Be hard to get.”

    BTW, your award is over at my new place,

  4. dating Says:

    There are 40 millionaire people using online dating. Choosing the right dating site from number of site can be daunting. And I suggest not to join an online dating site that’s free and doesn’t have a way of dealing with scam and Spam. I think niche dating sites is easier to find a date.

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