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3 Questions To Ask Divorced Dates


If you automatically reject matches who’ve been married before, you might miss out on a wonderful partner. Here, one expert explains how to suss out your relationship potential with divorced daters.

By Jen A. Miller

e’re sure you’ve already noticed that people have a few options to choose from when listing their relationship status on their Match.com profile. With about 40 percent of marriages ending in divorce, you’d be cutting out a huge selection of the dating pool if you automatically say no to those who ID themselves as separated or divorced. Good people
Move slowly into a relationship with a divorced person.
do make mistakes — or change — and want the opportunity to try again when it comes to committed relationships. Consider this statistic: 46% of marriages that end in divorce result in a remarriage for one or both people afterward.

But if you’ve never been married before — or even if you have — dating someone who’s recently divorced could be uncharted territory.

“Move slowly into a relationship with a divorced person, keep some sense of detachment until you know how grounded he or she is, and always use good boundaries,” says Tonja Evetts Weimer, author of Thriving After Divorce: Transforming Your Life When a Relationship Ends. She suggests asking three questions about your potential interest before moving ahead:

1. How long has this person been separated, divorced, or living apart from his or her former spouse?
There’s no set formula to determine how long it takes to heal a broken heart, but be wary if the person you’re interested in has jumped right back into the dating pool. As Weimer notes, “Breakups can be emotionally volatile, often irrational, and are certainly unpredictable. This person may truly believe that his or her past relationship is over, but strange things happen when newly single people start to date again.”

The best way to know if it’s right is to take things slowly — for everyone’s sake. “Don’t lay it on too thick. Don’t try to be overly romantic and serious,” says Christina, 30, who has never been married but has dated divorced men in the past. “Just be yourself and don’t try too hard. Relax, have fun and don’t expect too much.” Christina also suggests watching out for “serial wedders.” Last year, she dated a man who’d already been divorced twice by his early 30s. Soon after they broke up, he married again… not exactly what you’re probably looking for in your next date!

2. Is this person currently working on any emotional issues from his or her past relationship, or have they already been resolved?
Talking about a former relationship is healthy — as long as it’s not an obsession. “It’s important to your sense of happiness and stability that you not become someone’s therapist in this dating situation,” says Weimer. But that doesn’t mean you can’t bring it up, either. “Ask questions!” suggests Kristina, 39, who is currently in a relationship with a divorced man. “If there are
These aren’t exactly conversations that are appropriate topics for a first date.
signs that’s he’s not over it — such as constantly referring to the ex and items in his house or apartment — then make sure you have that conversation.” She also suggests asking about the reason for the divorce and whether he wants to be married again — “if that’s what you want,” says Kristina.

These aren’t exactly conversations that are appropriate topics for a first date, but if you are moving into a serious relationship, they are important to have at some point when you’re both comfortable with it. Don, 43, who married another divorcée two years after his own divorce was finalized, says that it’s important that the person has made peace with what happened. “While there will always be levels of bitterness towards an ex, there are those who accept that the divorce was in their best interest and are ready to move on,” he explains. “If someone is still obsessed by the failure of a marriage or felt that the divorce should not have happened at all, it’s time for you to politely move on.”

3. How does this person relate to his or her former spouse?
Being cordial with the ex isn’t necessarily a bad thing, especially if both parties have been separated for some time and/or have children together. “Is he or she civil and appropriate when talking about or interacting with the ex? If so, this is a good sign,” says Weimer. Monick, 35, is married to a divorced father of two and says that her husband’s good relationship with his ex-wife revealed a lot about his character. “The fact that they had a relatively drama-free and very kind and considerate relationship said a lot to me about him,” Monick says. “He treated her with respect and consideration, which boded well for how he would treat me.”

It’s the extremes you need to watch out for; if the former couple is too friendly, or they’re both filled with a lot of hate and vitriol towards each other, they might not be past the breakup just yet. Realize, though, that an ex-spouse will always be part of who someone is post-divorce — and don’t get in the middle of any disputes between the two of them. “Be aware and sensitive to the fact that the divorced dater has a history that may include children in addition to an ex-spouse. They will always be a part of the divorced person’s life,” says Pamela, 50, who has been divorced herself for 15 years. “Be supportive and stay on the sidelines while he or she interacts with their children and the ex.”

Both Pamela and Kristina prefer dating people who have been married before. “It can be a potentially satisfying relationship when you know the guy has already been in a long-term marriage and can commit to someone,” explains Kristina. For Pamela, who has children from her previous marriage, it’s almost a requirement: “How could anyone else possibly understand the closeness of a mother and her child or the joint parenting that we’ve managed to do (mostly) successfully for 15 years?” she says.

Once you’ve gone through this list of questions and had all the right conversations together, you’ll know whether or not the divorced person you’re seeing has real relationship potential or is still reeling from the emotional aftermath of divorce. With the right person, relationship mistakes that were made in the past will end up staying there — and you’ll reap the benefits of your partner’s personal growth and maturity.


Jen A. Miller is a NJ-based writer whose work has appeared in The New York Times, The Philadelphia Inquirer, Psychology Today, The Washingtonian and Men’s Fitness.
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