An interesting piece of feedback I hear from a lot of men and women who juggle working with a professional matchmaker, and dating apps, is how often their respective dates almost brag about how many people they date. This is a major “no no” when it comes to dating 101.
A friend I had a conversation with the other day mentioned that one man she is interested in, told her last year alone, he had over 350 dates with women. She chalked it up to being a Silicon Valley “data driven” type but the truth is, it’s not only daunting to imagine but a turn-off. 350 women! Who on earth has time for that unless unemployed and loving the hamster wheel lifestyle, yet with no real purpose or intention to settle down with one person?
My advice is not to talk about how much you have been dating recently. I think part of the psychology behind what fuels someone to mention all the dates they go on and people they meet is to showcase how desirable one is to the opposite sex. As in, the more I mention to him all the men that are emailing me for dates, the more he will think I am attractive.
The reality is, most of the time, if you share these conquests of sorts, you will appear as though you are not serious about finding a relationship. Instead, you’re in what I call “play mode” and not “serious mode.” There’s no denying play mode is awesome but be supremely careful with the information that comes out of your mouth and the image you project on dates. If you want to be taken seriously, you need to play the game right.
My advice is to focus on the man or woman who is sitting across from you on your date and show genuine interest in them. Be present, intentional, and motivated to find the right match with the “perfect” chemistry that works for you. If your date pokes around to see if you are actively dating and appears curious to hear stories, simply “don’t go there.” No need to lie or fabricate the truth but you can delicately switch topics with grace and dignity, while focusing on your date and not entering the slippery slope that is “TMI.”
Although the exterior looks great, your partner might just be a boy in a grown man’s body. Although we’d like to think age communicates a certain level of maturity, we all know it’s just a number; there will be 50-year old boys and 20-year old men. Maturity and self awareness—gifts that come with life experiences—separate the men from the boys. Here’s how to tell if you’ve found yourself dating a mature adult, or a boy who hasn’t reached full maturity.
Boys want to hook up, men want to invest in a real physical and emotional connection.
At some point, the thrill of the chase is just not that thrilling anymore when there isn’t a future. He may have been a playboy in the past, but if he’s ready for one woman, he’s stopped communicating with exes and flings. If he’s still chasing tail at the bars or toggling between dating apps, he’s not ready to commit.
Boys slink away, men spearhead difficult conversations.
If someone gets angry, is there silent treatment involved? If so, perhaps your partner hasn’t fully grasped the necessity of effective communication. Whereas boys might become passive aggressive or distant after problems arise, men will spearhead the issues directly. If you’re with someone who can accept criticism, apologize, and tell you if something bothers him, then you are dating a man with serious communication skills.
Boys need constant guidance, men handle their business.
If you’re dating a guy who needs you to carry him home after a night out or someone to make him apologize for losing his temper, you’re probably dating someone who isn’t fully self aware. A few wild nights are acceptable, a few wild nights that reveal your partner’s complete lack of self control or poor judgment indicate a lack of maturity.
Boys don’t think about their environment, men fine tune their living space.
This point might seem harsh and overly obvious, but how your partner lives reveals a lot about his personal habits. Grown men take pride in surrounding themselves with an environment that supports a healthy lifestyle. He might not live alone or have a lavish place, but you can tell he has invested in his surroundings.
Boys live in the moment, men are focused on the future.
A man who is ready to settle down will build a firm foundation—a way to support himself and take care of the people he loves. Although he’s living in the present, men tend to act with a nod to the future. Boys are more interested in the fleeting moments that have no real staying power.
Boys tear you down, men genuinely compliment you.
When boys feel insecure, they might resort to teasing or back-handed compliments to chip away at your confidence. Men, however, understand that a woman with self-esteem won’t respond to such behavior. If a boy finds himself overwhelmed by his overachiever girlfriend, he might want to downplay her accomplishments, whereas a man will not only embrace the success, but want to share her achievements with everyone.
After a string of unsuccessful dates, it can feel like you have a knack for attracting boys exclusively. Keep going; the right man is waiting for you and if he’s still not showing up, get in touch. We’d be happy to help.
After a bad date, string of bad dates, or zero dates, you might hear someone encourage you to try again with the old adage: “Dating is just a numbers game.” Sounds like a straightforward concept, but is there truth to this?
Although more dates increase the odds of meeting someone, you are not making the most of your dating experiences or your time unless you are learning more about yourself or figuring out a better picture of what you’re looking for.
MEN: If the “numbers game strategy” involves asking every woman you meet on a date in hopes one says yes, you are missing the point. However, if you are employing some level of discernment beyond visual cues, you are more likely to find a meaningful connection.
WOMEN: If your “numbers game strategy” involves going out with men with whom you haven’t had a single meaningful interaction but who are simply interested in you, you are setting yourself up for disappointment. Give yourself a chance to establish baseline connectivity before committing to a date.
When dating becomes a numbers game, it pushes us into a quantity over quality mindset, overwhelming our capacity to connect. One, it becomes easier to be more casual, passive about dating if each date is just an outing—not finding an opportunity to really connect. Two, you risk dating burnout. And, three, to achieve stronger, more meaningful interactions—the kind that last—we must know ourselves to filter potential candidates effectively.
Think you might be stuck on a lackluster romantic hamster wheel? Try asking yourself the following questions:
Does this person offer me chemistry and sustainability?
The chemistry makes things interesting, but what good is amazing chemistry unless it can lead to a deeper, enduring relationship? Unlike chemistry, the sustainability question requires logic. It may feel like you’re conducting an interview but getting clear answers on whether a potential partner is in a place—geographically and emotionally—to invest in a relationship will ultimately save you time and energy.
Am I aware of myself and what I am looking for?
Some of us carry negative habits and energy which can block our ability to receive and give love. Left unaware about the things we do to make ourselves less loveable will make it harder for a partner to connect. Furthermore, without knowing our blind spots, we won’t be able to select the right person to balance us.
Am I willing to take responsibility for the impact I have on another person’s emotions?
Taking responsibility for the way you date will make you more conscious about who you date. When you are deliberately seeking sustainable relationships, you’ll fine tune your ability to sniff out the relationships that don’t serve long term needs.
This guest post is written by Peter Nguyen, a private personal stylist for successful men and founder of The Essential Man
On our first date, my girlfriend and I went to PDT (above), a really cool speakeasy bar here in NYC hidden behind a phone booth in a hot dog shop. They’re known for their amazing cocktails, which we gladly put to the test.
If you asked my girlfriend about our first date, she couldn’t tell you much, except for one thing — the shirt I was wearing. A striped tabbed collar dress shirt from Robert Geller.
“It’s my favorite shirt on you.” She says.
It made such an impression on her that it has survived a good 5 closet purges.
You’ve probably heard the saying “It only takes 7 seconds to make a first impression”.
What if I told you you actually had less time than that?
According to a study done by Princeton, it actually only takes the brain 1/10th of a second to make a snap judgment of someone.
So what does this mean for you my single, dating friend?
It means that before you’ve even opened your mouth, she’s already sized you up. So it’s in your best interest to use the only tool you got in that brief, 1/10th of a second: your style.
BUT WAIT, THAT’S SUPERFICIAL! LOOKS SHOULDN’T MATTER! SHE SHOULD LIKE ME FOR WHO I AM!
Whenever I’m at a party and I tell people that I’m a personal stylist for men, I get one of three reactions:
1. “THANK YOU!”
(This is the #1 response from women.)
2. “Oh man. How’s my outfit?”
(This is where I try to decide whether to give the polite answer or the real answer.)
3. “Cool man. I don’t focus so much on superficial stuff like that.”
Yes, someone said this to me at a party recently.
Here’s how it went down:
“Interesting. What do you mean by that?” I asked him.
“Oh, no offense,” he said.
(I love when people say “no offense”, or “not to sound racist”. It’s usually followed up by something offensive or racist.)
“I want people to like me for who I am, not whether I’m wearing a nice suit or whatever.”
“Totally. Hey, it was great to meet you.”
And then I walked away to pour myself a much-needed drink.
(Conversation tip: Sticking out your hand and saying “Hey, it was great to meet you.” is the best way to leave a conversation you don’t want to be in.)
You’d be surprised how often I get this kind of reaction, especially when I bring up that one of the best “dating hacks” is to improve your style.
“She should like me for who I am!” Guys say in response.
“Ok.” I’d say. “Describe to me your perfect girl.”
What do you think their answer always is?
Their perfect girl is always HOT.
Yeah, shocker, right?
This is what I call “The Perfect Girl Hypocrisy”. People think they’re exceptions. They want everyone else to change their standards instead of raising theirs for themselves.
Obese people want to change health and beauty standards instead of shedding the excess weight. Unqualified job hunters want companies to lower their requirements instead of getting more experience. Guys want hot girls but don’t want to work on and be judged by their looks.
Sorry, my friends, it isn’t happening. That’s not how the world works.
THE UNCOMFORTABLE TRUTH ABOUT OUR LOOKS
Here’s the uncomfortable truth about humans: We judge each other by how we look.
Yes, it’s superficial. Is it bad? Maybe.
The thing is, we’re superficial about almost everything.
You’re less likely to eat sad looking food in disposable tins because we associate sad looking food with unhealthy. Judging by its looks, It’s probably not as nutritious and is most likely going to make us sick. (Even though this might not be true.)
Vibrant, colorful food on clean white plates symbolize to us freshness, cleanliness, and that it’s healthy to eat.
This is called Thin slicing — it’s making snap judgments on something based on the information you have at hand. When you don’t know a lot about someone, all you can judge them on is what you see. Presentation matters, whether it’s a plate of pasta, or what you wear on a date.
It’s the reason why when surveyed, 76% of patients found doctors who wore white lab coats more trustworthy.
If your doctor came in wearing an oversized shirt, messy hair, sweatpants and dirty shoes, would you want him looking at your kid? NOPE.
GOOD NEWS: IMPROVING YOUR STYLE IS EASY
Before you curse the world, let’s take something else into account. Your style is one of the easiest things you can improve when it comes to dating.
If you’re an introvert, it’s going to take a lot of practice to improve your conversation skills.
Unsure of your career and life path? Good luck changing that in a week.
Bad style? No problem. You can head to a menswear shop and do a complete 180 in 15 minutes.
Of course, you’ll need to know what to get. Luckily, I got your back.
I spent the last 5 months asking women around the world a question: What should a guy wear on the first date?
In total, I gathered 101 responses from women of all backgrounds, jobs, ages, and locations. Women from as close as New York City, to as far away as Tokyo, Sydney, and Tehran.
Here’s a brief overview of the women I spoke with:
Average Age: 28
Relationship (Less than 3 years) 29%
And here’s what they said:
#1. EFFORT IS THE MOST IMPORTANT THING
Does it matter if you’re wearing expensive designer clothes on a first date? No. In fact, of the 101 women surveyed, not one mentioned designer clothes.
However, the most common theme in the written portion of the survey? Above all else, effort (e.g. trying to look nice) was the most important quality of a man’s style on a first date.
Our style is a symbol of who and what we are. It represents choices that we’ve made in life.
Getting dressed is an action. And, as the saying goes, actions speak louder than words.
Does it matter what kind of car a father drives to pick up his kids? Of course not. What’s more important is that he shows up. It symbolizes that he’s responsible and cares for his kids.
“As a woman, I will make an effort to look nice and pretty for my date because I want to respect his company and effort for asking me out — and I would like the person to feel proud to be with me. When a guy dresses like a teenage boy and it looks like he didn’t care at all, it is distracting and really kills the first impression.” – Morganna, 27
WHAT YOU CAN DO TODAY: If you’re new to improving your style, check out my post “A Beginner’s Guide: 16 Essential Style Tips For Guys Who Want to Dress Better”
#2. THE RIGHT FIT IS MORE IMPORTANT THAN EXPENSIVE CLOTHES
Any clothing that doesn’t fit well is an instant put off. – Jennifer, 27
I’ve preached many times that getting clothes that fit will solve 90% of your style problems.
In my experience, men often wear clothes that are too big for them because:
- They grew up (like me) in a time where wearing baggy clothes was cool and never learned any better.
- They feel that it’s more comfortable.
Ill-fitting clothes wrecks havoc on your attractiveness. It makes you look fatter, shorter, and sloppy. Wearing clothes that fit properly not only makes you look better, it allows you to look good even when you’re dressed in something as simple as a t-shirt and jeans. (See: Ryan Gosling, above left)
If that doesn’t persuade you to wear clothes that fit properly, maybe this will:
Loose fitting [pants] remind me of my dad. – R, 24
There’s nothing that’s going to kill sexual attraction faster than that.
WHAT YOU CAN DO TODAY: Download my free “Style Starter Triple Pack”. It’s a combination of my 3 best guides, including my “How clothes should fit” cheat sheets that’ll help you master fit in 10 minutes.
#3. STYLE HACK: SWAP IN A BUTTON-UP SHIRT IN PLACE OF A T-SHIRT
60.2% of the women surveyed loved to see their date show up in a button-up collared shirt, while just 14.8% of women said they wouldn’t mind seeing their date in a t-shirt.
T-shirts are often associated with “casual” dressing. Swapping in a collared shirt signals that you’re putting an effort to go beyond “casual”.
WHAT CAN YOU DO TODAY: Not sure what kind of button-up shirt to get? Read my post on my favorite button-up shirt of all time “Essentails: The Chambray Shirt”
#4. SHOES? NOT AS IMPORTANT AS YOU MIGHT HAVE THOUGHT
This part of the survey surprised me the most, as I’ve heard time and time again that women will judge you based on your shoes.
Yet, when I asked women what kind of shoes they loved to see their date wear, the results were all pretty even.
A nice pair of boots won overall, but just barely, gaining 34% of the votes. The rest was split evenly between clean white sneakers, dress shoes, and “Other”, with the write-in answers consisting mostly of “it doesn’t matter”.
My recommendation? It’s hard to beat a solid pair of boots, as they can work with jeans or dress pants. My current favorite boots are from Thursday Boot Company, shown above.
And whatever you do, just don’t show up to your date wearing Vibram five finger shoes.
#5. WOMEN LOVE A MAN IN A NICE LEATHER JACKET
When asked what single piece of clothing would a woman love seeing her date wear, the clear winner was a perfectly fitted leather jacket.
A perfectly fitted leather jacket (50% of votes) beat a tailored suit (24.3%) by a little more than double, and completely crushed hoodies (2.8% of the votes, sorry readers in Silicon Valley).
If this doesn’t convince you to get yourself that perfect leather jacket, I don’t know what will.
WHAT YOU CAN DO TODAY: For those looking to add this essential into their wardrobe, check out my Ultimate Guide to Buying A Leather Jacket here.
#6. WHEREVER YOU GO, MAKE SURE THERE’S SOME ALCOHOL
While many women agreed that you don’t need alcohol to have a great first date (a few even said bar dates were uncreative and cliché) the data still showed they all wanted the option to drink. (Relax the first date nerves, perhaps?)
When asked what was their favorite place for a first date was, 65.8% of the votes went to places that had alcohol.
A nice cocktail bar received 27.8% of votes, a great dinner captured 25% of the votes, and a fun dive bar got 13% of the votes.
The remaining votes were split between coffee (19.4%), and “Other” (14.8%), which included write-in answers ranging from “it depends on the guy”, “a nice walk in the park”, and “a museum”.
OK, NOW WHAT?
Not sure what to do with this advice yet? Not to worry.
To help you out, I’m sharing with you some date and outfit idea combos based on this data to get your first date off to a great start.
THE MUSEUM DATE
Eyeglasses: Watts Eyeglasses by Warby Parker – $95, Wool Scarf: Acne Studios – $180, Blue Suede Bomber Jacket: Valstar – $1,135, Mandarin Collared Strip Shirt: FOLK – $185, Slim Fit Stretch Chinos: NN07 – $160, Socks: The Workers Club – $40, Boots: Thursday Boot Co. – $199
The Date: Museum dates are a great way to break up the monotony of meeting up a bar, but it requires a bit of strategy.
The biggest mistake you can make on a museum date? Spending a lot of time looking at the art and reading the text! I know, it doesn’t make sense, but hear me out. First dates are all about getting to know each other. When you’re examining the art and reading at a museum, you have a tendency to be quiet. The real focus of your date isn’t the art, it’s your company. Think of the museum like a beautiful backdrop, just the same as if you were strolling through a park.
- Grab a map for you and your date.
- Next, walk and talk, glance at the art, but don’t stop, especially to read the text. That takes away from precious time to get to know each other.
- After the initial walk through, take a break at the museum café, order some food, talk some more, then pick parts of the museum you want to have a second look at together on the map.
- Go back to the spots you chose and enjoy the art.
- Don’t forget to stop at the gift shop and pick up something nice. (Like the wallet from the MoMA above.)
The Outfit: The key items in this look are the collared shirt and boots. Wearing a suit on a first date, especially something like a museum, can feel like overkill. You want to communicate that you’re putting a little effort into it, and this is why instead of a t-shirt and sneakers we swap in a button-up shirt and boots. Blues and browns are a great color combination that help you stand out, especially if you’re visiting a museum in NYC where everyone loves to wear black. Give it a pop of color with a bordeaux colored scarf.
THE NON-CLICHÉ COCKTAIL BAR
The Date: I love a date at a cool speakeasy, but securing a spot at one can be stressful, especially on a first date. There are plenty of cocktail places with great stories that don’t require you to search for a hidden, unmarked door – like Bar Goto, a Japanese bar opened by ex-Pegu club alum Kenta Goto. Order his signature Sakura martini – a blend of gin, sake, maraschino liqueur finished with a beautiful sakura blossom. (Photo above)
The Outfit: The polo is the happy medium between a t-shirt and button-up shirt. The key to not looking like your dad is picking one that’s slimmer cut in a non-traditional color, like this sleek Lanvin number. Slip on sneakers can sound like an odd choice at first, but like the polo, we’ve elevated it. This suede model from Common Projects isn’t your 16-year-old brother’s Vans, and gives a nice casual contrast to the formal dress pants. Bordeaux and charcoal gray is my all time favorite color combination. It’s warm and romantic, paired with a sleek black leather racer jacket, you’ll be hard to forget.
THE LOW-KEY DINNER DATE
Cashmere Coat: Suit Supply – $699, Brushed twill shirt: J.crew – $39, Watch: IWC – $3,950, Wool Drawstring Pants: Acne Studios – $350, Embroidered wool scarf: Paul Smith – $225, Socks: FALKE – $28, Derbys: A.P.C. – $455
The Date: Dinner on a first date can sometimes feel like a trap. What if you realize you two aren’t really into each other and your entrees just came? Instead of a proper dinner for a first date, I recommend getting some wine and tapas.
Tapas are small plates of appetizers and snacks that you share over drinks. I love it because the tapas themselves become a conversation point. Decide on ordering things you’d never normally try, get adventurous. Start with a few plates and see how things go. If it’s going well, you two can order more and keep the date going. Not feeling it? No worries, you share a few bites and don’t have to commit to a conversation over an entire entree. Grab the check and part ways.
Some recommendations for you first-time tapas eaters: Dátiles con beicon (dates stuffed with almonds and cheese, wrapped in bacon) and patatas bravas (crispy potatoes with an aioli) are easy crowd pleasers. My all time favorite: Jamon Iberico, slices of ham from pigs fed acorns then aged for 36 months. Fatty, nutty, and worth the (very expensive) price.
The Outfit: Suits on first dates is a little too much. Subtle style substitute – wear a tailored topcoat. It gives the same feeling that you “dressed up” without going full blown suit.
When I think tapas, I think sharing food, drinking wine, having an amazing conversation. So take off your coat and relax a little bit. You’re going to be moving plates around and passing food to her, so don’t be afraid to unbutton and partially roll up your sleeves. This is a great opportunity to show off a nice watch. My pick: IWC’s refined entry Mark XVIII. It’s a watch that says “I have really good taste and I don’t need to be flashy”.
GET THAT SECOND DATE
First dates are like movie trailers, a preview to get her interested and excited and make her want to see more.
While I’ve armed you with some style tips to make sure you look your best, remember that clothes don’t make the man, they just enhance him.
To make sure you kill it on your first date and get her asking when can she see you again, I’ve put together a free bonus guide for Linx with some of the best first date tips.
The point of the first date is to discover if there’s real compatibility beyond initial interest. If she’s already said yes, consider yourself off to a good start. If you want to give yourself the best chances of romantic connection—or even a second date—consider the chivalrous route. Here are 8 things gentleman do on first dates that prove chivalry is not dead.
Suggest a first date in a place convenient for her.
Instead of suggesting the restaurant or bar closest to you, you ask what is most convenient for her. Your asking demonstrates consideration and shows that you are willing and able to make her life easier—a feeling that will ultimately make her feel more relaxed during the first date. Same logic applies when you ask about any food allergies or preferences she has. Any research you do before the date will benefit you exponentially.
Observe the 4 p.m. deadline.
If you have plans tonight, text or call to confirm your date by 4 p.m. Many women start wondering if the date is still on, especially if a few days pass between the ask and the event. A short text to the effect of, “Looking forward to seeing you tonight. Let me know if we need to adjust the timing” will keep everyone on the same page.
Mind your (table) manners.
Follow behind as you make your way to the table; she should not be walking in your wake. When you get to the table, ask if you can help her check her coat. At the table, let her order first. Letting her take the lead shows that you are want to make sure her needs are met before yours. This simple gesture is another way you can ensure she is comfortable. Lastly, always encourage a glance at the dessert menu. There’s nothing more sexy than indulging in the senses and enjoying the rich decadence of chocolate. Even if you’re not a dessert guy, order one to share.
Should you run into friends on your date, be sure to introduce your date without saying “my friend”. There is no need for an extensive introduction, but you must acknowledge your date if a friend says hello. You could say, “I’d like you to meet [date’s name]. We were both excited to try this place.”
Mind the Drinking.
Pay attention to what she orders and offer a refill when the glass is empty- same principal goes for her water glass. Even though your nerves may want to order a third drink, stick to a two-drink maximum. Slurring your words is not classy.
Pay the bill.
That’s right. Let’s keep this equation simple. Be prepared to foot the bill and keep any conversation surrounding this transaction to a minimum. If she offers to pay, politely decline and change the subject. Paying for her is a sign of interest and shows that you are happily willing to invest when you have feelings. If you both continue to date, it’s very appropriate for her to reciprocate at some point but definitely not on date one.
Offer to get an Uber for her.
When a simple gesture that takes 2 minutes can make all the difference, you should do it. Let her know that you’re interested in getting her home safely, whether that means you ping Uber or offer to drive her yourself.
Close out the evening with a text.
There is nothing gentlemanly about leaving a lady to wonder if she’ll hear from you again. Thank her for her time and company and, if you want to see her again, let her know. Be confident in your actions and consistent with your communications to the woman you’re interested in.
With holidays approaching, you may find yourself wanting a relationship more than usual. As the days get shorter and the weather cools down, singles are looking for a relationship that will tie them over the next few months, but perhaps not endure into the spring. This heightened desire for a semi permanent relationship occurs during “Cuffing Season”.
Cuffing season begins during that stretch of fall when the weather begins to cool off and everyone you know starts coupling up. It specifically describes the desire to couple up or “cuff” ourselves to a partner during the chilly months—and stay together until spring. The trend is undeniable, but what causes it? Is this preference to cozy up just a preference or are we biologically engineered to get monogamous during the cooler months?
Is “Cuffing Season” actually real?
Short answer is yes—winters yield a higher rate of conception; spring yields changes to Facebook relationship statuses. When Hinge, a popular dating app, polled users, they discovered that men were 15% more likely to look for a relationship in the winter than any other season. Women were 5% more interested in a monogamous relationship, too.
Is “Cuffing Season” the result of biological impulses?
Experts agree that although people tend to pair up during winter months, the urge to couple up is not substantiated by any biological impulse. In fact, humans have evolved to a point beyond mating seasons. Scientists note that humans associate cold temperatures with loneliness, which could prompt the urge to get monogamous, but ultimately, the need to “cuff” ourselves to each other isn’t a biological or evolutionary response.
So, how do I handle the “Cuffing Season” urge?
Those urges to couple up aren’t easy to avoid. Between plus-one invites and fears of experiencing the holidays alone, you might find yourself approaching relationships from a place of neediness instead of real affection. Make sure the chemistry is real by taking any relationship you start this winter on the slow side. Gift giving, family travel, and plus one invites might add a little more complication to your dating life than usual. Don’t let the stress of the holidays rush your love life. Remember, spring is right around the corner.