Dating Tip: Avoid Excessive Bragging

A major no-no is bragging or name-dropping. Oh, you saw Robert De Niro at the Starbucks this morning and you get your hair cut at the same place as Meryl Streep? Might be an interesting story for your friends over brunch, but isn’t exactly going to impress your date.

Along with keeping name-dropping on the shelf, also put any desires to brag away, too. You may have a yacht the size of Yankee Stadium, but “casually” slipping that into the conversation is not only tasteless, but is bound to make you look desperate, too. You want your date to fall for you because of who you are, not what you can offer them as far as superficial and materialistic things go.

Avoid Looking Needy or Like You're Fishing for Compliments

Avoid smothering your date with compliments by saying such awkward things as “I’m so lucky to be on a date with you.” Think about it: how would you feel if someone said that to you? You’d probably think the person in question either had low self-esteem or was fishing for compliments themselves.

While it’s fine to be appreciative and gracious toward your date, don’t do so at your expense. Everyone has something interesting to bring to the table, and being aware of the parts of yourself that others will find intriguing will help you stay away from any “woe-is-me” type comments. And honestly, no one wants to be put up on pedestal—it’s dangerous up there and people tend to fall from them quite easily.

-Estelle
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Estelle is the president/owner of Estelle Matchmaking, LLC a boutique matchmaking service for selective singles in the NYC area (including Westchester and Fairfield Counties) and South Florida.

Become a Person People Want to be Around

Just because you’re successful in your job, it doesn’t mean you’re well-rounded. In enhancing yourself and your passions, you’ll make yourself a more interesting and compassionate person.

Consider volunteering or looking into a hobby that you’ve always meant to investigate and do so with gusto. Passionate people exude passion on all levels, and those who give back to their community are better for it. This isn’t to say you’re not a good person now, but people can always be better and there’s always room for improvement.

-Estelle
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Estelle is the president/owner of Estelle Matchmaking, LLC a boutique matchmaking service for selective singles in the NYC area (including Westchester and Fairfield Counties) and South Florida.

A Positive Attitude is So Important When Dating

Be in a good mood. What puts you in a good mood? A certain song? Watching Love Actually on repeat? Whatever it is, do it before you leave for your date. You want to be happy and charming; you also want that feeling to be contagious. It’s hard to fake happy, so if you’re not actually feeling in a good mood, you may want to consider rescheduling for the sake of everyone involved. If your heart and mind aren’t in the right place, your temperament is bound to be sour, too.

-Estelle
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Estelle is the president/owner of Estelle Matchmaking, LLC a boutique matchmaking service for selective singles in the NYC area (including Westchester and Fairfield Counties) and South Florida.

Cell Phone Etiquette While On a Date

Nothing says lack of interest louder than keeping your phone out and answering or texting mid-dinner. In this day and age when technology is literally in the palm of our hands, do your date the favor of tucking the electronics away.

If you’re on call or expecting an important phone call and absolutely must have your phone out, perhaps you should reschedule for another time. People go on dates for conversation and getting to know someone, not to hear one side of a conversation you might be having on the phone. Ideally, just turn it off until the date is over… this may be shocking, but it will still be there when you’re done.

One exception may be if you have young children at home and want to make sure you are reachable in case of an emergency. In that case, setting your device on “vibrate” mode and leaving it in your pocket may be the best alternative.

-Estelle
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Estelle is the president/owner of Estelle Matchmaking, LLC a boutique matchmaking service for selective singles in the NYC area (including Westchester and Fairfield Counties) and South Florida.

First Date Mistakes (What to Avoid)

Don’t choose the most expensive restaurant out there. Similarly to the tip that advises against bragging, a very expensive restaurant can put the same negative impression out there. You don’t know the financial situation of your date, so while you’re thinking you’re looking like Mr. Fancy Money Bags in your restaurant choice, you may actually be making your date feel uncomfortable, and in the end, you’ll look a bit foolish.

-Estelle
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Estelle is the president/owner of Estelle Matchmaking, LLC a boutique matchmaking service for selective singles in the NYC area (including Westchester and Fairfield Counties) and South Florida.

More Table Manners and Dining Etiquette Advice for Dating

Don’t eat too much or too little. If you eat too much during dinner, you may come off looking as though you starved yourself all week for this one meal, and if you eat too little, you may seem uninterested in the date and/or wasteful. A happy medium is always the best route when it comes to dining out. This doesn’t mean you can’t order an appetizer before your entrée, it just means that you should be aware of your presentation—and that goes beyond your physical attributes and carries into the actual dining part of the date.

Here are some more dining tips:
Don't Drink Too Much
Make Time For Dessert
The Dinner Date
Proper Restaurant Behavior
Eating Etiquette

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Estelle is the president/owner of Estelle Matchmaking, LLC a boutique matchmaking service for selective singles in the NYC area (including Westchester and Fairfield Counties) and South Florida.

Romantic Restaurants in New York City, Perfect for Your Date!

You should opt for a quiet and romantic (but not too romantic) restaurant in the early stages of your dating process. You want a place where you can hear your date and be heard by them. What’s the point of being charming, if the person across the table from you can’t appreciate your sense of humor because of all the noise? An intimate restaurant choice is key in learning about your date.

Here are a few restaurants I suggest that offer ideal dinner atmospheres:
ABC Kitchen
Family Recipe
Degustation
Flex Mussels
Due
The Mermaid Oyster Bar
Centro Vinoteca
JLOB
Hangawi
Candle 79
Peasant
Salumeria Rosi Parmacotto
Sfoglia
Tori Shin
Boulud Sud

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Estelle is the president/owner of Estelle Matchmaking, LLC a boutique matchmaking service for selective singles in the NYC area (including Westchester and Fairfield Counties) and South Florida.

How to Look Beautiful for a Date

Go for the heels, ladies. Not only do the majority of men love high heels, but they do wonders for your figure, accentuate the calf muscles and can even make larger feet appear smaller as well.

According to such experts like Jimmy Choo, a high heel is anything 3.5 inches and above. If you’re not used to wearing high heels, consider practicing around your home until you get it down to a science—they really make you look leaner and more sophisticated. And when you pair them with that little black dressed we’ve suggested in early tips, you’ve made yourself into a stunning knockout.

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Estelle is the president/owner of Estelle Matchmaking, LLC a boutique matchmaking service for selective singles in the NYC area (including Westchester and Fairfield Counties) and South Florida.

First Date Beauty Tip: Don't Wear Too Much Makeup

Studies have shown that although a lot of makeup may seem attractive at first, over time, women who wear too much of it are perceived as being untrustworthy. Similar to your attire, be conservative in your makeup look—go for something that’s slightly more dramatic than you’d wear to the office. You may think sparkle eye shadow will make your blue eyes pop, and perhaps, they will, but you’re going on a date, not to Carnival in Rio.

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Estelle is the president/owner of Estelle Matchmaking, LLC a boutique matchmaking service for selective singles in the NYC area (including Westchester and Fairfield Counties) and South Florida.

Who Pays on a Date?

Although feminists will probably cringe, the man should pay on the date. As we covered on this blog before, prove that chivalry isn’t dead. Along with being a gentleman in your gestures, also pick up the tab. This may be the 21st century, but tradition is still appreciated by most, if not all women.


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Estelle is the president/owner of Estelle Matchmaking, LLC a boutique matchmaking service for selective singles in the NYC area (including Westchester and Fairfield Counties) and South Florida.

First Date Dating Tip: Don't Drink Too Much

You may fancy yourself as someone who can hold their alcohol, and this may be true, but a date isn’t the place to show off what your learned at the frat house in college.

Do not have more than two drinks all evening. If you’re going out for drinks after dinner, then fine; but if your date ends with dinner, then you should keep it to one drink total. You may know for a fact that there’s no way in hell two drinks is going to make you sloppy, but you can never gauge the tolerance of someone else—not just with alcohol but with drinkers in general. If you want to get silly on too much champagne, save it for further into the relationship. Besides, you really don’t want to deal with a hangover the morning after when you should be recapping what a great time you had and planning your next date.

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Estelle is the president/owner of Estelle Matchmaking, LLC a boutique matchmaking service for selective singles in the NYC area (including Westchester and Fairfield Counties) and South Florida.

Talking Too Much is a Turn Off on a First Date

And breathe… seriously, breathe and don’t cut your date off. Breathing is, well, essential to living, and gives your date a chance to share parts of themselves, too. While we covered not monopolizing the conversation in an earlier tip, keep in mind that on top of allowing your date to share the stage, you also don’t want to interrupt or cut them off either. The only thing worse than not letting someone have a voice, is shutting them down mid-sentence. Although you may have something to say and want to make sure you do so before you lose your thought, take a breather, a bite of your filet mignon, a sip of your wine—whatever it takes to make sure you don’t silence your date.

-Estelle
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Estelle is the president/owner of Estelle Matchmaking, LLC a boutique matchmaking service for selective singles in the NYC area (including Westchester and Fairfield Counties) and South Florida.

How to Ruin A First Date

Maybe it’s been raining for the last week or the Dow just dropped to an all time low, keep the negative talk out of the equation. If it means searching deep inside your soul to find light topics that don’t focus on whatever might be ailing society at the moment, do it. Try listening to “happy” music on the way to your date to uplift your spirits. You don’t want to bring down the conversation, and negative topics are the first way to kill a mood and a date that may have been going swimmingly otherwise.
-Estelle
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Estelle is the president/owner of Estelle Matchmaking, LLC a boutique matchmaking service for selective singles in the NYC area (including Westchester and Fairfield Counties) and South Florida.

Make A Great First Impression On a Date

Be yourself. Yes, easier said than done, but if you have a strong sense of self, once you get over your nerves, you should be able to settle into your actual and true personality. Don’t try to be someone else or make jokes that are inappropriate, because even a stranger can tell when someone is putting on pretenses. Sure, jokes are fine, but make them jokes that you, the person you are, would tell. There’s no worse injustice than not being you.

How to Handle a Goodnight Kiss on the First Date

The chemistry is there, the connection has been made, dinner was amazing and you’ve walked and laughed for hours afterward, now it’s time to say “good night,” so what next? Proceed with caution, that's what.

Although things may be sailing along, you don’t want to push your welcome or rock all the good progress you’ve made during your date. A way to avoid coming on too strong and making it seem like your intentions are more physical than they are, is not trying to kiss your date. Even if the moonlight is perfect and the moment seems right, do not lean in for a smooch on the lips. Kissing on the cheek when you say goodbye is completely acceptable; anything beyond that is a “no-no.” People hold their personal space in the highest regard, overstepping those boundaries is no way to end a date that was great.

One Bit of Crucial Dating Advice

Do not, under any circumstance, forget your wallet. Before you leave for your date double check to make sure you have your wallet. Nothing is more embarrassing than the check arriving, you reaching to pay, but coming back with an empty palm.

While you may think you’d be able to remedy the situation by calling a friend to swing by your place and grab your wallet for you, that’s usually the stuff of romantic comedies and life isn’t so ideal. Honestly, this mistake could be an unforgivable one and guarantee that you never see that particular date again—no matter how great it may have gone up until that point.

Make Time for Dessert on Your Dinner Date

Once the dinner is over, don’t rush your date out the door. Dessert is the sweetest part after all! Be courteous enough to realize that perhaps your date may want to end the meal with dessert and/or coffee, so make sure you put that option out there. Proper meals don’t end at the entrée and another course is more time to get to know the person sitting across from you.

-Estelle
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Estelle is the president/owner of Estelle Matchmaking, LLC a boutique matchmaking service for selective singles in the NYC area (including Westchester and Fairfield Counties) and South Florida.

Risky Discussion Topics: Politics, Religion, Finances and Sex

They say you can’t argue politics and religion, and it’s true. Politics, religion as well as finances and sex fall under “risky” topics especially if this is your first time going out. Depending on where you and your date fall on the spectrum of these matters, you just might be setting yourself up for a debate of which you were not prepared.

To avoid such pickles, steer clear of discussions that are one-way tickets to controversy. You don’t want to force your date to throw down their napkin dramatically and head for the door, because you thought it might be interesting to talk about your thoughts on the GOP and they didn’t agree with you on Rick Perry’s policies.

-Estelle
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Estelle is the president/owner of Estelle Matchmaking, LLC a boutique matchmaking service for selective singles in the NYC area (including Westchester and Fairfield Counties) and South Florida.

The Dinner Date is Essential in the Courting Process

Commit to “breaking bread.” Traditionally, the breaking of bread is steeped in a history of celebration and the beginning of relationships. To decide on just drinks or coffee is limiting yourself from perhaps finding someone that just might be a great fit for you.

While both men and women occasionally express a fear of committing to an entire dinner because they don’t want to be “stuck” with someone that’s not working out, it’s important to keep your mind open. Don’t ever think of yourself as stuck. There’s nothing wrong in taking time out of your life to meet someone new; even if you feel “it’s just not there,” in the initial few minutes, those feelings may change by the end of the evening. In passing up dinner and opting for a casual drink, you diminish your chances of getting to really know someone.

Some love coaches blame the fact that people are putting the dinner date off as a reason why there are so many singles out there. They also cite that just a drink lowers the level of enthusiasm and romance. Marriage starts with courtship and the dinner date is essential in that courting process, so do both you and your date a favor and insist on dinner.

-Estelle
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Estelle is the president/owner of Estelle Matchmaking, LLC a boutique matchmaking service for selective singles in the NYC area (including Westchester and Fairfield Counties) and South Florida.

3 Best Flirting Tips

Flirting is the best way to show you’re interested and having fun; it’s also a difficult task for some. There’s a fine line between flirting and taking the technique to an awkward extreme. Keep these few suggestions in mind:

1. Smile. Smiling shows you’re happy and having a good time, so show off your pearly whites.
2. Laugh (but not at everything). If you laugh at everything that’s being said, especially at your own jokes, you may want to take it down a notch. Excessive giddiness can make you come off too desperate to please your date. Laugh when appropriate, and laugh genuinely. Fake laughs are the worst and, honestly, kind of insulting, too.
3. Make physical contact. While reaching for a knee mid-flirt can be interpreted as inappropriate and definitely over the edge, a light touch on the arm or hand shows comfort and sincerity.

-Estelle
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Estelle is the president/owner of Estelle Matchmaking, LLC a boutique matchmaking service for selective singles in the NYC area (including Westchester and Fairfield Counties) and South Florida.

Never Ask Too Many Personal Questions When First Dating

Do not pry. Although it may be going well and you’re feeling comfortable, keep in mind that the first few dates are not the place to go looking for skeletons in someone’s closet. We all have our secrets and it’s when we’ve truly reached a level of trust that we let someone into our secret world. Asking your date personal questions that they may not be ready to answer is not only invasive, but also rude.

-Estelle
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Estelle is the president/owner of Estelle Matchmaking, LLC a boutique matchmaking service for selective singles in the NYC area (including Westchester and Fairfield Counties) and South Florida.

Dating Advice for Men: Women Love a Gentleman

While some my say “chivalry is dead,” prove your date otherwise. Make sure you get the door, walk your date to the subway or a cab, even hail a cab and make sure your date is safely in it and on their way home. It may seem like a foreign concept, but if you want to win points with your date, go so far as to stand up every time she leaves or comes back to the dinner table. Chivalry is a lost art so be a gentleman and practice it.

-Estelle
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Estelle is the president/owner of Estelle Matchmaking, LLC a boutique matchmaking service for selective singles in the NYC area (including Westchester and Fairfield Counties) and South Florida.

Picking the First Date Location

Be willing to compromise when it comes to the area of town where you’ll be meeting for your date. If you’ll be coming from opposite ends, suggest a place somewhere in the middle, but be open to input. There are two people on this date and making sure each party is comfortable in the neighborhood choice is one way to get things off on the right foot.

-Estelle
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Estelle is the president/owner of Estelle Matchmaking, LLC a boutique matchmaking service for selective singles in the NYC area (including Westchester and Fairfield Counties) and South Florida.

How to Compliment Your Date

Perhaps, you find yourself on a date with a real “looker,” that doesn't mean you have to ogle. Compliment your date politely and keep from staring at him or her as if you’ve never seen someone so breathtaking; even if you haven’t, show restraint. No one wants to be looked at as if they’re a piece of meat. Look at them genuinely and respectfully, and use complimentary adjectives the same way. Telling someone they’re “hot,” isn’t the best way to win them over – be far more eloquent and creative in your word choice: beautiful, elegant, sophisticated, etc.

-Estelle
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Estelle is the president/owner of Estelle Matchmaking, LLC a boutique matchmaking service for selective singles in the NYC area (including Westchester and Fairfield Counties) and South Florida.

Give Your Date Room to Speak

Studies have proven that for most people their favorite topic of conversation is themselves. You may think you’ve had the most fascinating life and you’re just sharing, but give your date room to speak, too. A conversation is dialogue made up of more than one person; if you monopolize the situation, you’re pretty much just talking to yourself and coming off self-involved, as well. Frankly, if that’s how you want to spend your night—talking about yourself only—you could have just spared your date and stayed home. Walls are great for one-way conversations.

-Estelle
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Estelle is the president/owner of Estelle Matchmaking, LLC a boutique matchmaking service for selective singles in the NYC area (including Westchester and Fairfield Counties) and South Florida.

Proper Restaurant Behavior When Dating

Be kind to the wait staff. If the service at the restaurant you’ve chosen is lacking a bit and maybe not up to par, remember your manners and use them. No matter how much you may want to make a scene and demand to speak to the manager, that’s a first impression you just don’t want to make. Always say “please” and “thank you” when it comes to service people – even if it means doing so with gritted teeth.

Also don't forget to tip and tip well! A lot can be said for those who tip generously--they're not only un-stingy, but they're grateful and understand that being in the service business is actually a really tough job.

-Estelle
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Estelle is the president/owner of Estelle Matchmaking, LLC a boutique matchmaking service for selective singles in the NYC area (including Westchester and Fairfield Counties) and South Florida.

Don't Discuss Past Relationships With Your Date

Whether or not you’ve had your heart broken or you’ve done the breaking, a date is not the place to rehash your former relationships. Even if what you could have done differently is still in the forefront of your brain and perhaps, you’re looking for “insight” from the opposite gender on the matter, just don’t bring them up. It’s not only a downer, but liable to make you look as though you’re unable to move on with grace and confidence. In other words, leave emotional baggage at the door.

-Estelle
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Estelle is the president/owner of Estelle Matchmaking, LLC a boutique matchmaking service for selective singles in the NYC area (including Westchester and Fairfield Counties) and South Florida.

Dating Tip: Eating Etiquette

This one may seem like an obvious one, but some people have yet to understand that when you’re eating, your mouth should remained closed at all times. First of all, no one wants to witness what’s bouncing around on your tongue; secondly, there’s a good chance some of your dinner may fall out; and thirdly, your mother told you long ago it was rude. FYI: your mom was right. Even if you’re excited to answer a question or respond verbally, continue to chew, then swallow then speak.

-Estelle
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Estelle is the president/owner of Estelle Matchmaking, LLC a boutique matchmaking service for selective singles in the NYC area (including Westchester and Fairfield Counties) and South Florida.

Don't Be Controlling: First Date Advice from a NY Matchmaker

No one likes to be told what to do, especially on a first date. Although you may think you’re doing your date a favor by “suggesting” they not order a specific dish, you’re more than likely going to come off a bit controlling. As someone new to their life, you don’t know what their taste buds might be craving, so although you may think you’re just being friendly or helpful, stop while you’re ahead. One man’s Kobe beef, is another’s burger.

-Estelle
Estelle is the president/owner of Estelle Matchmaking, LLC a boutique matchmaking service for selective singles in the NYC area (including Westchester and Fairfield Counties) and South Florida.