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Dating After Divorce

In the midst of a period that is generally filled with turmoil and heartache, a bright spot is that, by moving on from a relationship that didn’t work for you, you now have the chance to find somebody new. For many people who have been married for quite some time, the new dating game may seem overwhelming. Not only has it been a while, but now there are dozens of apps and dating rules that can be confusing and intimidating. In the most recent Ask Lloyd, we talked to a professional in the dating field, Michelle Jacoby owner and Chief Connection Officer (our words not hers!) of DC Matchmaking. She had some excellent advice and insights to share.

The Three Be’s of Dating Again

1. Be Ready

Before jumping back into dating, Michelle thinks it’s critical for a newly single person to get right with themselves. Focus first on being happy alone and feeling good about life. Too many people start dating too soon to fill a void, which leads them to put too much emphasis on the missing piece (e.g., family or financial stability) instead of making the right match. She recommends doing some work on yourself with therapy and focusing on letting your family adjust to the new normal before looking for love.

2. Be Positive

There are a lot of reasons why it might be tempting to talk about your divorce and your ex when you go out on a date. Don’t. Positive, healthy people are forward-looking, and they are looking for a kindred spirit who isn’t stuck in a bitter past. You may think you need to “justify” your divorce by explaining why it wasn’t your fault that it didn’t work out, but studies have shown that when you talk negatively about someone else, you are perceived more negatively as well.

3. Be Strategic

The strategy may sound less than romantic, but it’s important to have a plan before dating. Start with assessing what needs you had that weren’t met in your prior marriage, and be honest with yourself about those that were. Then take a look at your preferences. What’s the difference? A need might be financial responsibility, while a preference is good looks or snappy dressers. Be clear on both, because needs are deal breakers, and preferences are not. Michelle works with her clients on a protective contract – an agreement you make with yourself that you won’t settle for a partner who doesn’t meet specific needs.

So, What are the Rules?

We were curious whether there are any rules about when and who to date, but Michelle made it clear that it really depends on the individual. In terms of timing, she emphasizes that you need to be in a positive space because toxicity doesn’t lead to good outcomes. Some people are looking for a new life partner, while others want to keep things casual. Neither preference is better; it just matters where you are with yourself. Her one piece of advice is to wait before getting physical. Michelle points out that it is better to connect emotionally and intellectually with the right person. She points out that the impulse to determine “compatibility” can be achieved by a couple who have a basis of trust and communication to work through that issue if it happens.

We were so grateful to Michelle for her insights. Many people going through a divorce are nervous and excited about moving past the old relationship and exploring something new. With some self-reflection, it is possible to get out there and find the right match. For Michelle’s complimentary book visit here.


Malech Law is located in downtown Bethesda, Maryland. For more than 25 years, Mr. Malech has provided aggressive and effective representation for his clients in Maryland and the District of Columbia. This year, he was selected as the Best of Bethesda 2022 Readers’ Pick for Best Family Law Practitioner. He has also been given the Lawyers of Distinction Award Recognizing Excellence in the Area of Divorce and Family Law for the past three consecutive years and has just been recognized as a Family Law Top 10 Attorney for 2021 by “Attorney and Practice Magazine.”

Visit Malechlaw.com or call (202) 441-2107.

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