Getting Around Town With Jamie Shupak: Extending a Summer Fling

Getting Around Town With Jamie Shupak: Extending a Summer Fling

Jamie Shupak is the Emmy-nominated traffic reporter for NY1, the Big Apple cable network that’s the end-all and be-all on all things Gotham for New Yorkers. She’s also a beautiful, single woman navigating New York’s treacherous dating scene after the painful breakup of a 10-year relationship. In her weekly column she’ll share her war stories and offer her advice and admonitions.

Days are getting shorter; nights are getting cooler. You’ve probably said it more than a handful of times today: I can’t believe it’s September. But does the end of summer also mean the end to your summer fling?

Not necessarily.

Sometimes hot-weather hookups are meant to be temporary, and as soon as that first fall breeze blows on the back of your neck you’re ready to say goodbye to your beach beauty. If that’s the case, then no matter how short or hot the fling, at least do so gracefully.

But what happens if you find yourself feeling something a little more for your bikini-clad babe? Like the stamp on the suntan lotion you’re ready to toss after Labor Day, does every sun-scorching affair have an expiration date?

I think if you like her enough and want to take it to the next level, go for it; you’ll never regret trying. Here are a few ways to go about turning that tropical tryst into something more serious.

Take Off Your Rose-Colored Ray-Bans

Summer is a relaxed, easy time of year. You and your fling probably spent a lot of time in picture-perfect settings, feeling great because you were at the beach, on a boat, or sitting by the lake. The colder seasons—real life—mean stress, deadlines, and worst of all, more layers of clothing keeping the two of you apart. If you want to take your summer love into the next few seasons, you need to realize things will be different. Just like there are certain sides of yourself you haven't shown her, you’ll be encountering new sides of her that you’ll have to get used to. 

Not everything is as simple as it is in the summer. Remember that and keep an open mind when her schedule isn’t as accommodating, when she’s not showing as much skin, or she begins to cling to you a bit more as the temperature drops.

Go On a Real Date

If you want your summer fling to turn into something more serious, the most important thing is to take her on a real date. Meeting for drinks and going back to your place is not a real date. Neither is having her meet you and your friends at the sports bar and taking her home from there.

What you need is pre-planned, one-on-one time. Call her and ask her out—yes, pick up the phone and dial her digits—but first make sure to have a spot in mind where you can easily make conversation. It's important to find out if the two of you share common interests besides boating, barbeques, and pool parties. Connecting on more than a physical level is key to carrying the summer lovin' on into the rest of the year.

Make a Plan for the Fall

If you think your relationship—or whatever you’re not calling this—has post-summer potential, make plans to attend an event in the fall. Go to a concert or football game. Or go apple picking, or to a winery, or to a quaint bed and breakfast with hiking trails nearby.

Nothing shows a little commitment—or at least the attempt at it—like buying tickets or making plans more than a week in advance. You’re also showing her that you’re capable of having fun year round, not just at your boy’s share house in the Hamptons. But you’re thinking, What if we don’t make it to that planned date? Well, if the relationship disappears like footprints in the sand before the event rolls around on the calendar, bring your boy who ran that Hamptons house. You probably owe him anyway.

Introduce Her to Your Friends

Do your boys approve? One way to see if it’s worth extending the expiration date on this fling is to gather your best bros, hit a beer garden or park for the day, and invite the girl. Don’t bring her to a crowded bar or some place that will make it hard for her to hear everyone, because you want to give her a fair chance to feel comfortable. After all, she’s most likely only seen you after a few cocktails, or when she has backup of her own in the friend department. So put her at ease and make sure your friends are acting to your benefit—not hitting on her or bombarding with her odd or inappropriate questions. If she aces this friendly showdown by being cool with your friends— and them, her—it’s a great sign that this has a chance to last.

Tell Her How You Feel

If you don't let your crush know how you're feeling now, you may never get the chance to tell her again. Don't just assume that the relationship has a September expiration date, or that she’s done with you. Let your summer fling know you’re into her and that you want to see where things can go. Women love a guy who’s direct and says how he feels. Sure it’s a daring move with the possibility of rejection, but the risk may be worth it.

Look on the bright side. If your feelings aren’t reciprocated, there’s always next summer.

Next Week: Jamie discusses bad date redemption: is it possible?


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