Post-divorce dating topics

If you’ve recently jumped back into the dating pool, your skills at making first-date conversation are probably a bit rusty. Unsure whether topics such as your ex, your kids or your divorce are safe to discuss with someone new — or better kept under wraps? Below, seasoned post-divorce daters offer some of their own road-tested talking points that helped them make a good impression during their own first dates. Read on...

Discuss these five safe (yet insightful) subjects with your date:

Your interests and those of your date

“The whole point of a first date is to get to know the other person — what better way to do it than to discuss the things you enjoy doing, right? If he or she enjoys similar things, great — if not, at least you’ll know soon when to cut your losses. If you’re not ready to reveal too much about yourself, why not let your date do all the talking? I always ask a lot of ‘So tell me about yourself, your job, where you’re from, etc.’ type of questions. I’ve never met a woman reluctant to talk about herself, and I always get a good sense of who she is.”
– Brad, 40, Austin, TX

Your chosen career field

“A topic that always comes up on a first date is what you do for a living. The topic can get a little dull, so I try to talk about how I got into my line of work and what I’d like to be doing career-wise in five or 10 years. I like to ask the same questions of my date, too. I feel like going beyond a simple ‘This is what I do’ explanation makes it more interesting and fun to talk about.”
– Carson, 44, Denver, CO

Your feelings about the activity you’ve chosen for this date

“Sometimes, making conversation on the first date can be awkward because you’re not entirely comfortable opening up about yourself — especially if you haven’t dated in ages. If you’re nervous or unsure about how much of yourself you’re willing to share, focus the conversation on what you’re doing together on your date. For example, if you’re at dinner, talk about what you think of the restaurant’s ambience, the food or the service. If it’s a movie, after it’s over, engage your date in a discussion about what you both thought about it. Even though you’re not revealing personal stuff about yourself, in a roundabout way, you still will be — and so will your date.”
– Maria, 39, Natick, MA

Where you’re from and what growing up there was like

“I always like to discuss where I grew up and ask my date the same question. I like to go beyond the whole “I’m from Cleveland” thing and talk about what my parents did, the kind of school I went to, the types of activities I did in school and in college, etc. I don’t go into so much detail that it’s boring, but I think it’s always interesting to let someone know a brief bit of your history and vice versa.”
– Sarah, 37, Orlando, FL

Your favorite movies, music and books

“I like to bring up what I call ‘lighter side’ topics, which means subjects that don’t carry a lot of emotional weight. My favorites are movies I’ve seen lately that I loved, books I recently read and loved or a great album I just bought and enjoyed. I like to see whether my date agrees and if he has similar thoughts to share regarding his own entertainment preferences. That usually opens up a discussion about our favorite movies or music, which I always think is a good indicator of someone’s personality.”
– Kara, 39, Baltimore, MD

Avoid these five off-putting topics while chatting with your date:

Financial issues, especially those related to your divorce

“It’s never good to talk about your financial situation or the financial aspects of your divorce — i.e., who got what, how much, how little, how stressed you are about it, etc. Not only is it nobody’s business, it’s just such a sensitive topic that you’ll probably make your date feel uncomfortable — not to mention suggesting that you’re all about money.”
– James, 36, New York, NY

Your inability to get along with your former spouse

“Nothing makes you look worse — or more bitter — than trashing your ex. Even if he or she is a terrible person, it just makes you seem like the person who’s difficult to get along with. Before you open up about this topic, make sure you’ve been on enough dates with this person that he or she will have a true sense of who you are and recognize that you aren’t the ‘bad’ guy or gal.”
– Ashley, 33, Lexington, KY

Your children (to the exclusion of everything else)

“Of course, your kids are an important part of your life, but don’t focus on them too much. It’s never a good idea to avoid bringing them up, because you definitely want a sense of your date’s receptiveness to the fact that you’re a parent. However, remember that a date is ‘adult time.’ Let the conversation focus on ‘adult’ topics centering around you and your date, not just on your kids and their activities.”
– Amalia, 41, Charlotte, NC

Your strange family dynamic

“Granted, everyone has their own family drama, but a first date isn’t the right place to share that information. It could freak out your date, or scare him or her out of ever wanting to meet — or even become — part of your family. Plus, it doesn’t demonstrate a whole lot of loyalty or ability to maintain a sense of privacy.”
– Jenelle, 35, Beaumont, TX

How your date compares to your ex

“Good or bad, telling your date how he or she compares to your ex is never a good idea. Not only is it bad form, it’s never a good idea to judge someone new against a bad experience. Instead, evaluate your date based on who the person is and not how he or she compares to your ex.”
– Marc, 47, San Jose, CA

When DC-based journalist Chelsea Kaplan isn’t helping you solve your relationship problems, she’s making jewelry. Check it out at

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