Cuffing season is in full swing and first dates are warming hearts like chestnuts roasting on an open fire.

It’s also the season where singles are finding themselves stuck in a one-date-wonderland, wishing and hoping that first dates will turn into a second or even a third. Sound familiar? If so, this is not the time to get discouraged! As Matchmakers & Dating Experts, we know that the more first dates you go on, the more likely you are to find the relationship you are looking for.

So, grab a cup of cocoa and cozy up on the couch while we walk you through how to stop coasting through the one-date-wonderland, so you can make that right turn onto lover’s lane.

Make your first impression last! Everyone knows that you have one chance to make a first impression. And rarely in dating do you have a chance for a first impression “do over”. So, with slim to no chance at a “do-over”, it’s to your benefit to know that creating a great first impression starts BEFORE the date even occurs. Two easy ways to create a lasting first impression are all in the planning.

First, be punctual. Planning a grand entrance or not, the most important thing you can do is to make sure that you are on time. The more time your date has to wait on you, the more time they have to overthink the date which calls for an awkward hello followed by excuses - none of which make someone attractive (and it’s just simply rude).

Second, dress to impress. One of the biggest attraction factors is effort. Make sure it looks like you put in effort - or that you just look that good effortlessly. When you look good, you feel good, making you more attractive to your date!

Act Interested AND Be Interested. It’s important that you aren’t spending most of the date monopolizing the conversation or making your date feel like they are in an interview. They don’t want to work for you, they want to date you! Make sure you are asking questions and finding out about them. Let them talk, so you can find commonalities and share experiences that are relatable and draw them into fun conversation banter. A great conversation is always better than playing 20 questions. Neither of you are there just to check off boxes or to hear yourself talk!

Also, you should ALWAYS make your date feel like they are the only one in the room, or at least the most important. Because, when done correctly, it’s a secret weapon to ensure a second date.

Make Yourself Available Availability is two-fold. There’s physical availability and emotional availability. When you are serious about wanting a relationship, you need to make time for one. Working with busy professionals at It’s Just Lunch, we prep our clients to set aside time to date or be flexible when they meet someone.

But physical availability is only half the battle! During your dates, show that person across the table that you are available to have someone in your life.

Secure Date #2 on Date #1 You know what they say… “The good ones go, if you wait too long”. At the end of the date, talk about another date - or at least make sure you are communicating you are interested in seeing them again. Or take the leap and ask them, and get it on both of your calendars. Imagine the relief of knowing you are meeting up again soon, and not playing any games. Second dates are the key to knowing you’re not missing out on the love of your life.


It's time to get out of that one-date wonderland for good and prepare yourself for a snowfall of seconds this holiday season. The path to a relationship is one date/one match away!

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