Post-divorce Dating Milestones

Here’s advice on four dating moments that, after a big breakup, can have your scratching your head and asking, “Now what?!”

By Nina Malkin

ou’ve aced the quick coffee meet-up. You’re cool with dinner and a movie. Even a Saturday afternoon bike ride is delightfully doable. What’s next? Four significant “milestone” dates may ensue—and as a recently single person, you could probably use a refresher course. Here’s how to ace these signpost social encounters to ensure further relationship progress.

1. The at-home date.
It sounds easy—you and your date
If the date is at your place, clean up to make a good impression.
opt to hang out at your place or his/hers.

What it means: You like (and trust) each other enough to test this comfort level and bring the relationship from public to private. The at-home date is also illuminating. “You can learn a lot about the person’s interests and lifestyle by seeing your date in his/her environment,” says Andrea Syrtash, author of He’s Just Not Your Type (and That’s a Good Thing): How to Find Love Where You Least Expect It.

How to ace it: If the date is at your place, clean up to make a good impression: Do a walk-through to make sure there’s nothing sitting out that you wouldn’t want your date to see. If you’re the guest, don’t show up empty-handed. (Flowers are always nice, wine if you’re coming for dinner, or a book you think he/she would like.) The general guideline is to avoid grand gestures. If you want to cook, cool, but keep it simple. Or if you discovered that you’re both Scrabble fanatics, break out the board. Consider an at-home date with a built-in time limit—for instance, invite the person over for cocktails before heading to hear some music. That’ll take the “what do we do next?” pressure off.

Bonus tip: Back in the day, an invite to “come up and see me” was a euphemism for “let’s have sex.” While no longer necessarily the case, where there’s a bed, there’s a possibility. So if you’re not at all ready to sleep with this person, defer hanging at home. If you’ve entertained the notion, be prepared to make the encounter a safe one.

2. Meeting the friends.
So it’s been a while since you’ve done anything like it, but it’s time for a double or group date… or to attend a party where many of your friends (or your date’s) will be present.

What it means: You like this person enough to bring him/her into your social circle (or you’re liked enough for such an introduction). It’s also a great way to get to know someone. “You’ll learn a lot seeing this person interact with others,” says Tina B. Tessina, Ph.D., author of The Unofficial Guide to Dating Again. Still, it can be daunting, since you know there’ll be some scrutiny, perhaps even comparisons to the ex.

How to ace it: Keep the event casual. “No one wants to feel like they’re on display, so make the meeting as easy-going as possible,” says Syrtash.
If you’re not at all ready to sleep with this person, defer hanging at home.
“Meet for drinks after work or do an activity, like bowling, to alleviate some of the pressure.”

Bonus tip: Ignorance is not bliss, so help your date feel at ease with conversational inroads, such as telling a friend, “Susan, Pete’s from Atlanta just like you,” or “Ronnie, you might want to talk to Ava about camping. She really loves the outdoors.” When you’re the newcomer, focus on being interested, not interesting. You don’t have to show off. Instead, get to know the people who are important in your new sweetie’s life, advises psychologist Paulette Kouffman Sherman, Ph.D., author of Dating From The Inside-Out: Using The Law of Attraction in Matters of the Heart.

3. Impromptu sleepover.
It can be all fireworks and magic, but few dating situations are as ripe for comedic or mortifying memories.

What it means: Odds are, it’ll be a little weird in the sober light of day. “You feel awkward or nervous because you didn’t plan this,” says Dr. Tessina. “One or both of you may feel ashamed or embarrassed after.” In other words, ideally first-time sex should be a conscious decision, but don’t beat yourself up too much. Unplanned trysts happen more often than you probably would think.

How to ace it: Don’t be caught unprepared. Carry condoms and keep them at home, and if it’s been a while since you’ve used them, relearn! Basically, that’s the only rule. “There is no right way to do this,” says Dr. Sherman. “Just enjoy being close, and try not to get ahead of yourself. Make your date feel welcome, and remind yourself how sexy you still are.” Relax and have fun. “You have a right to be spontaneous,” reminds Syrtash. Let honesty and humor break the morning-after ice. Simply saying, “Gee, this is awkward!” works. If neither one of you needs to rush off, consider having coffee together, but there should be no expectation that you’ll spend the whole day together.

Bonus tip: Be kind and reassuring, even if you don’t want to see the person again.

4. Weekend away.
A mini-vacation can bring you closer.

What it means: This relationship has real potential! “You’re asserting the fact that you like spending time together so much that you want to enjoy each other’s company in a new environment,” says Syrtash. The simple fact that a getaway involves more planning than an ordinary in-town date shows you find each other worth the effort.

How to ace it: Don’t rush into this extended rendezvous. “Build up to it so you’re not blindsided by habits, attitudes or personality quirks you didn’t see before,” says Dr. Tessina. Pick a place you’re both psyched to see and/or an activity you’re both into doing—in your effort to please, don’t agree to a sailing trip if you get seasick in the bathtub! Remember, too, that people have different traveling styles. Just because your former spouse could do a museum in 45 minutes doesn’t mean the new person in your life won’t want to spend the whole day.

Bonus tip: Get on the same page in terms of exclusivity—and not in regard to the resort you visit. “Your date may believe a weekend trip signifies commitment, and you might not be thinking the same thing, or vice versa,” says Dr. Tessina. There should be a mutual understanding about this before you go to avoid disappointments. If you clear that hurdle, go and have a great time!

Nina Malkin is the author of An Unlikely Cat Lady: Feral Adventure in the Backyard Jungle.
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