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.