Get Out There Again

10 rules to keep in mind before you take that all-important step—and get out there again.

By Chelsea Kaplan

hat’s scarier than going on your very first date ever? Going on your very first date after a divorce. To help make the big event run smoothly, we gathered advice from men and women about how to survive — and thrive — when you’re ready to start dating again. Here are guidelines and some true stories that back them up.

Rule #1: Put some effort into your outfit
“When I was married, I got used to throwing on any old thing—I felt like I had no one to impress. So when I went on my first date after my divorce I
Be sure you’re really ready to date again.
wore beat-up old khakis and an un-ironed shirt. My date was dressed to kill, and I felt like a total mess. Remember, when you start dating again, you’re trying to impress someone so look the part.”
—Josh Kantor, 39, Warwick, RI

Rule #2: Give yourself a recovery period
“My divorce had only been final for a couple of weeks when I went on my first divorcee date. I guess I was still reeling from the split because I spent the majority of the time talking about how much I hated my ex. I didn’t realize it until my date said, ‘Wow, sounds like you’ve still got a lot of issues to resolve. Are you sure you’re ready to be dating?’ He was totally right. After about six months, I had a new attitude; I had let go of a lot of my anger, and was finally ready to channel my efforts towards meeting someone new. And that was the right time to start dating again.”
—Paula Franklin, 42, Minneapolis, MN

Rule #3: Don’t get hung up on age
“I was reluctant to date older women because I thought they wouldn’t be as much fun. But the first woman I went out with was 40, and she was extremely successful and worldly. I found her to be incredibly self-assured, confident and sexy. It was like a totally different ball game—no games and no drama. Older women have a defined sense of self, and they know want from life—both of which are fantastic qualities.”
—Craig Hersset, 34, Villanova, PA

Rule #4: Don’t feign an interest
“For my first post-divorce date, I agreed to a baseball game, claiming I loved baseball in order to wow the guy I was going out with. The truth was that I hate sports; I had never been to a game and knew nothing about baseball. When we got there, he kept making references to the game and asking my opinion, and it soon became clear that I had lied. Of course it was my lying that turned him off, not the fact that I didn’t like baseball.”
—Dawn Webb, 36, Highland Park, IL

Rule #5: Don’t go to an old haunt
“I think I had become so accustomed to my ex-wife’s love of seafood that I scheduled my first post-divorce date at a restaurant we used to go to together. We had a fine time, but the wait staff kept asking where my ex wife was. Needless to say, the date wasn’t a success. I never went there again—alone or with a date!”
—Larry Grossberg, 38, Edgewater, NJ

Rule #6: Don’t put all your cards on the table
“I guess it had been so long since I’d dated, I wasn’t sure how to act. Within the first five minutes of my first date, I explained my whole history, laid out
Take it slow and let your story unfold as time goes on.
exactly the type of person I was looking for, and explained that I wanted to remarry. My date was clearly freaked out. Now I know that a date isn’t a job interview. Take it slow and let your story unfold as time goes on.”
—Shelley-Ann Poole, 33, Hartford, CT

Rule #7: Don’t kid around
“About an hour into my first date after my divorce, my date mentioned that he was so glad that he and his ex never had kids because he ‘just wasn’t a daddy type.’ I have two young kids, so I knew immediately that there was no possibility of our ever having a relationship. What a waste of a Saturday night and a babysitter! I figured that having kids wouldn’t be that big of a deal to a fellow divorced person, but to some, it is. After that date, I made sure to be very up front — beginning with the date-planning stage — about my status as a parent so that I didn’t waste anyone’s time… nor have mine wasted.”
—Ann Reese, 38, Pittsburgh, PA

Rule #8: Plan an activity-based date
“Your first post-divorce date is a big step! I recommend choosing a fun, active event like going to an amusement park or the zoo over meeting for dinner. In an ‘activity-focused’ situation, there are fewer opportunities for awkward lulls in the conversation because you can always talk about what you’re doing or seeing. Even if your date is a dud, you’ll feel more at ease.”
—Joe Tallston, 40, Millwood, NJ

Rule #9: Don’t be afraid of branching out
“I had never been into dancing before my divorce—my ex-wife never particularly enjoyed it, and I never thought I was very good at it. When my date, Sarah, suggested we go swing dancing for our first date, I tried as hard as I could to get out of it, but she wasn’t having any of that. Good thing she persisted—I had a blast! I think dating after divorce — especially that first time — is really about opening yourself up to new possibilities, so don’t be scared to do things you never would have considered in your ‘former life’!”
—Eric Donnelly, 37, Los Angeles, CA

Rule #10: Keep the conversation focused on the future
“I always advise not discussing your ex on that first date. It’s too much of a reminder of the past when you’re trying to move forward. Instead, talk about the things that you find interesting and alluring — your interests, your goals for the future, your travels, etc. — and ask those same questions of your date. After all, isn’t your ex the last person who should ‘be’ on that date with you?”
—Laura Wellborn, 33, Detroit, MI

Chelsea Kaplan is deputy editor at The Family Groove. Her work has been featured in Self, Men's Health, New Woman, Bridal Guide, and The Mommy Times.
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