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6 Surprising Dating Milestones


These moments together may seem like no big deal, but they’re actually major opportunities to strengthen your bond. Here’s how.

By Kimberly Dawn Neumann

hen you’re dating someone new, there are all kinds of memorable firsts: The first kiss. The first time you exchange those three little words. The first time you meet the parents, and they adore you (of course). You expect these pivotal turning points... and know what they mean to your relationship. Still, there are a host of other firsts many couples ignore—the ones that you almost didn’t notice were momentous occasions until much later on.

These unexpected dating milestones, and how you handle them together, can determine how your couplehood evolves. So keep an eye out for these turning points, and keep this advice in mind to make the most of them.

Milestone #1: The first time something embarrassing happens
You know the scenario: You’re out with someone you’re digging and suddenly you split your pants, fall off the curb, spill your glass of wine down your shirt, or are otherwise
The first time you decide to get together with absolutely no plan is a major step forward in your relationship.
trying to be cool and end up looking like a dork. “Once, on a first date when the guy went to use the restroom, I reached under the table to grab my bag and accidentally set my hair on fire on a candle. I immediately patted out the flame but was horrified,” says Cindy Marchionda, 30, New York, NY. “But this guy was so sweet, we had a good laugh about it when he got back. He even kissed me goodnight in spite of the singed hair smell.”

The moral of the story? Watch how your date handles this snafu. “If you’re out with someone and you laugh and the soda you were drinking suddenly comes out of your nose, your date’s reaction can make all the difference,” says JoAnn Magdoff, a psychotherapist and relationship expert in New York, NY. At the moment the cola bubbles are burning the inside of your nose, you need a little commiseration and a napkin, not signs your date’s even more uncomfortable about it than you. “If this relationship has potential, your date would have to think it was kind of cute and reassure you when you’re feeling embarrassed,” says Magdoff.

Milestone #2: You get together with no concrete plans
Usually dating consists of an agenda. There’s the dinner-and-a-movie date, the picnic-in-the-park date, or maybe the drinks-and-dancing date. So, the first time you decide to get together with absolutely no plan is a major step forward in your relationship. “I knew my current boyfriend and I were a hit when, by our third date, we had no idea what we’d do,” says Stephanie Young, 26, Oklahoma City, OK. “We just met at his place, hung out in our sweats and watched the tube. Our immediate comfort level made me realize he might be The One.”

Why is this a big deal? “This sort of time, spent without a specific goal, is a great indicator that you really like this person,” explains Magdoff. “Instead of feeling like you have to accomplish something, you’re effectively saying ‘I feel comfortable enough to do nothing other than just be with you.’” So go ahead and ignore that little voice that might crop up saying, Shouldn’t you be entertaining each other? If you like to bury yourself in the Sunday paper without feeling compelled to make idle chit chat, stick to your guns—after all, sooner or later your honey will see the real you. Why not start now?

Milestone #3: Major career stress tears you apart temporarily
What happens when suddenly your couple-time is replaced by overtime thanks to a cranky boss, major project or otherwise demanding career issue? While severe cutbacks in together time may seem like the beginning of the end, riding through this workaholic wave can do wonders for your relationship. “When I was studying for an additional bar exam, I was literally physically and emotionally unavailable to my beau for two months. If I wasn’t in class, then I was locked behind closed doors studying or sleeping,” says Regina Petruzzi, 32, from Pittsburgh, PA. “But in spite of the fact that I was neglecting him, he knew that getting licensed was important to me. In the end he was so proud of my effort — and I of his patience — that it brought us even closer together.”

If your sweetie’s office hours are making you feel blown off (or vice versa), it’s crucial to have a talk about it so the neglected party doesn’t jump to the wrong conclusion. “The person who’s working long hours should reassure the other person of the security of their relationship,” says Magdoff. Likewise, dates who feel deserted should take pains to avoid guilt-tripping their dates to wedge in time for them. “You have to learn to accept who you’re with and what are likely to be the demands on him or her,” says Magdoff. “It’s not that this relationship isn’t the most important thing in the world to your date — it very well might be — but it’s not the only thing.” So be realistic, and don’t take it personally if your amour has other things on his or her plate for awhile.

Milestone #4: The first time one of you gets jealous
Maybe it’s harmless flirting with another hottie. Or a realization that the very idea of anyone else touching your date makes you crazy. Whatever the case, that first glimmer of
When your date drops by out of the blue and you feel happy rather than hassled, a relationship shift is definitely in the works.
jealousy can definitely move your dating relationship in a different direction. “The upside of jealousy is that it prompts questioning,’” says Magdoff. “Usually it ends up with stuff like, ‘Do you want to date other people or not?’” In other words, if the little green monster rears its ugly head, don’t be surprised if the conversation veers toward seeing each other exclusively—or, if you’re already an item, it can show your date he or she means a lot to you, which is also sweet!

The key, of course, is to not fly off the handle, but to ask what the deal is before drawing drastic conclusions. And likewise, your date shouldn’t get defensive but see your concern as a sign that you care. Jody Reynard, 28, from New York, NY, knows this all too well after she accidentally found a condom in her boyfriend Dan’s backpack. “I immediately went to this crazy jealous place thinking, Who is he seeing? How can he do this to me?” she recalls. But when she asked about her discovery, “He just laughed, reassuring me that he hadn’t unpacked since the last time he’d been away on business, which was before we were even dating! He felt he should always be prepared for the unexpected when he traveled. When he realized that I was jealous, he thought it was adorable, hugged me really tight and told me that he loved me.”

Milestone #5: The first time your date stops by unexpectedly…and it’s OK
Picture this: You’re in your pajamas, your place is a disaster, dirty dishes in the sink… and your newest amour knocks on your door for an I-was-just-in-the-neighborhood-and-thought-I’d-drop-by visit. If you feel happy rather than hassled, a relationship shift is definitely in the works. “It reminds me of drinking from someone else’s water glass at a table. It’s not something you do unless you feel really close,” says Magdoff.

How do you know if your relationship has reached drop-by status? It’s certainly not something to try early on, and you should wait for cues like the other person saying, “I miss you,” or “I wish you were here,” during phone calls or emails. Or, rather than pulling a 100-percent surprise drop-by, try calling when you’re five minutes away so your date has a chance to refuse (or accept and do a quick cleanup). And if you’re on the receiving end of a visit and embarrassed about your pigsty of an apartment, know this: Your date isn’t thinking about the dirty dishes in your sink or the fact that you’re in sweat pants. He or she is thinking how nice it is to see you. “The first time my girlfriend, now fiancée, surprised me with an unexpected house call my place was a mess,” says Alexander Newman, 33, Reston, VA. “But instead of being grossed out, she threw her arms around me. I realized we were at a new place in our relationship because we weren’t trying to hide our flaws from each other. It was now OK if she showed up and I was in my boxers, eating pizza and playing Xbox.”

Milestone #6: You survive a trying/traumatic situation together
Maybe one of you faces a health scare or a relative or beloved pet dies. Though trying situations can be hard, facing one as a duo can also be very bonding. “It can actually be a ‘deal-maker,’” says Magdoff. “If you’re unsure about someone and then you see this person handle a tough situation well, you might think ‘Gee, this is what the long haul is about.’ There is not a right way to behave when faced with a tough situation. What’s important is that you work together to get through it.”

Byrd Schas, 30, from New Haven, CT, experienced this epiphany with her boyfriend Peter when, after a few months of dating, she was forced to endure major spinal surgery. “He was an absolute angel the whole time,” she recalls. “He came to see me every day. He put up with all my demands and crankiness. He was so loving and devoted — never once complaining about being my manservant — that I knew ours was a relationship that would last. We’re getting married in October.”


Kimberly Dawn Neumann is a New York City-based freelance writer whose work has appeared in Cosmopolitan, Redbook, Marie Claire, and Maxim.
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