Making Your Valentine's Date Great

Every year, as February approaches, men and women everywhere start pondering that one special date night of the year – each one looking forward to that evening with a mix of hope and trepidation. In his defense it’s a lot of pressure and effort for one night. In her defense, she’s probably had enough bad dates to last a lifetime. This year, partner with Downtown Middletown, designated one of the most romantic main streets in America, and let’s get it right.

From the invitation to the kiss goodnight, we’ve got you covered. Between now and Valentine’s Day we’ll features lots of advice followed by several Valentine’s date ideas. You’ll find tips on how to invite her for the romantic evening, what sort of gifts might leave a “wow” impression, and how to make sure that you create a perfect and positively memorable evening for your date.

Tip 1: Know your date

Whether you just met her last month in English Lit, or you’ve been married for 20 years, knowing your date is absolutely critical. It’s the first tip, because this one takes time for observation. Everyone wants to be known, to be noticed as an individual, someone special. Does she go gaga for a hot fudge sundae, or are pedicures more her thing? What’s her favorite flower or is chocolate the way to her heart? Does she wear pink all the time, or have you glimpsed her black fingernails? Does she love to cook, dance, sing, rollerblade, or kickbox? Who is her favorite cartoon character or does she prefer classical literature? Make a list of everything you’ve noticed or casually heard her say in passing. Maybe her teddy bear collection is her pride and joy, or perhaps she’s mentioned that she has always wanted to take trip around the world. Noticing these small details and incorporating them into romancing your date will speak volumes. And believe me, there are ways to incorporate almost anything. I once knew a man who showed up to a date with Hershey syrup and a funnel. The woman had jokingly mentioned that she could drink a bottle of that stuff straight. Without saying a word, he was loud and clear.

Tip 2: Make the evening about your date, not about you.

The biggest mistake in dating is to take your date on your dream date. If you love professional basketball, but your girl loves the theater, don’t take her to a game – at least not if your intent is to impress her. Most likely, if you show a deep interest in the things that interest her, she will return the favor, and she might even score some great seats at an upcoming game for you. Girls don’t typically mind going along and participating in his passions, but finding a guy who will participate in hers is a rare gem – and all girls want is to find a guy who will tell her with his actions that SHE is special. Now that you’ve studied your date and you think you know what she is interested in, you’re already ahead of the game. You can plan a date from A to Z with her in mind.

Tip 3: The First Impression

While not always necessary, the way you invite your date can set the stage for a romantic evening and set the expectations at the right level as well. Don’t text it. Don’t post it on your date’s Facebook page. You can go as casual or as formal as you’d like, but whatever you do it will send a message. It will tell her how well you know her, how much you think of her, and it could also set the stage for a great theme date. Want to invite him to playful date and make him feel like a kid again? Pass him a note with check boxes like you might have in middle school. Inviting her to a romantic Italian dinner? Serenade her or send her a heart shaped pizza from Papa Johns with a note inviting her on her Valentine’s dream date. Want to take her on a dessert tour? Send her a cupcake with a little flag sticking out the top with your message on it. Planning an artsy date? Paint him a picture or chalk his driveway with the details. There are thousands of ways you can ask him or her out, but choose wisely because first impressions are important.

Tip 4: Be Prepared.

On any date you want to make another person feel special. You want to make them think or feel about you in the right way too. There’s no way to plan for every imaginable challenge, but you can prepare for many of them. If you’re going out on Valentine’s Day, call ahead for the menu and make a reservation if possible. You’ll know if they’re serving a special selection for the evening or their regular menu and you’ll be prepared for the prices too. Have plenty of quarters handy for parking meters. You don’t want your date digging through her purse looking for quarters. If you’re going dancing, stash a couple band-aids in your wallet just in case she gets a blister or two from those sexy heels she wore to impress you. Make sure there is an umbrella in your car, an ice scraper because this is Connecticut, and have a back up plan or two as well just in case something goes wrong. It’ll help keep you calm and cool no matter what disaster looms on your date. And always have at least two or three questions to ask her. The more open ended, the better. They make great conversation starters for those moments when the awkward silence might otherwise creep in.

Tip #5: What to Give?

Valentine’s Day is supposed to be the most romantic day of the year, right? It’s the date when your special someone should say he loves YOU in a myriad of ways. Then why is it that instead stores fill their shelves with one-size-fits-all gifts of chocolates and red roses? No store or advertising gimmick should have to tell me what the “right” gift is to give or receive. I don’t know when or how chocolate and red roses became the standard but the fact that it has become the standard somehow makes it feel pretty generic – like maybe he didn’t know which girl he was actually picking up tonight so he went with the one-flower-fits-all red rose. Maybe your date loves red roses, in which case get those, absolutely. However, if she loves orchids or irises or daisies, get her those instead. If you don’t know her favorite flower but you know her favorite color, run with that! If you know she has allergies, consider a bouquet from Edible Arrangements. Maybe she loves chocolate and there are loads of varieties to choose from, but try to get her something that says you’re paying attention to her more than the ads on television. From classic corsages to couple's retreats, Downtown Middletown has it all.

Check back here for more advice, date ideas and our Valentine's Gift Buying Guide - all coming soon!