Dating after divorce? Take this advice from a relationship expert

There's a phrase that best describe the feeling many people have when they begin dating after divorce: Scary as hell.
by Jackie Pilossoph / / Source: TODAY

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There's a phrase that best describes the feeling many people have when they begin dating after divorce: Scary as hell.

Putting yourself out there after marriage or a long-term relationship has ended, can make you feel uncomfortably vulnerable. This is especially true now that the number one way in which couples connect is by looking at thumbnail-size photos of each other, reading a two-sentence description of the person and swiping right or left.

As a relationship columnist, I have a few pieces of advice to offer and I stopped by Megyn Kelly TODAY to chat about this topic. Whether you are recently divorced or broken up, or you’ve been divorced and single for awhile, here are some tips that might help prepare you for a better, smoother dating experience.

1. Ask lots of questions on your date.

Let’s be honest: A date really is like an interview. You are trying to learn more about your date to see if he or she is a good fit for you. Many people get nervous on dates, and as a result talk, talk, talk about themselves. Not only does their date end up feeling like they couldn’t get a word in, but the talker never gets to learn about the other person.

2. Don’t focus too much on your divorce or your ex.

Your date doesn’t want to hear about how your ex is a jerk or isn’t adhering to the terms of your divorce agreement. If you talk negatively about your ex, or call him or her a four-letter word, you will most likely never hear from your date again. If your divorce does come up, try to keep the conversation brief, and try to refrain from using these words: depressed, heartbroken, devastated, bitter or deadbeat.

3. Ask yourself two key questions.

“Does he bring out the best in me?” and “Do I like myself around him?” These determine if he or she is a good fit for you. I once dated a man who made me feel bad about myself when we were together. I was constantly trying to get him to love me, and he just didn’t. Instead of continually trying to make it work, tell yourself he or she isn’t the one, that it isn’t personal and that you need to move on for your own well being.

4. Don’t talk too much about your kids.

Our children are our pride and joy, and they are in most cases, the most significant part of our lives. That said, your date isn’t with you to talk about them the entire time. He or she is there to get to know you, and what defines you outside of being a parent.

5. Have fun.

Enjoy yourself and take it lightly. Don’t put pressure on yourself to find your next spouse. Take things slowly and let them evolve authentically.

6. Laugh about bad dates.

If a date turns out to be a nightmare, there is almost always a funny story to tell. Let yourself laugh about it! Also, no date is ever a waste of time. Try to find something good that came out of it.

7. Do not look at your phone during the date.

Unless you are checking on your kids, put your phone in your purse for the night!

8. Watch how your date treats the waiter.

If your date is rude to the staff at a bar or restaurant, you are seeing only the tip of the iceberg. Run fast!

9. Don’t drink more than two drinks.

After two cocktails, I find that most men and women become looser. While this can be a good thing, too loose can be dangerous. The alcohol might cause you to say or do things you wouldn’t normally say or do.

10. Don’t have sex on a first date.

I don’t feel this way because I’m old fashioned, I just think sex changes the entire landscape of the relationship way too quickly, and there is a whole part of flirting, foreplay and friendship that could get covered with lust and clouded emotions.

11. There are no “buts” in a healthy, happy relationship.

If you’re dating someone and your friends ask, “How’s so and so?” and you say, “Good, BUT ...” that is an indication that there could be issues. When it is truly right, you will stop after “good.”

12. Be understanding.

Remember that divorced men and women are juggling a lot: kids, jobs, an ex and more. Dating is very different than when you were younger. Last-minute cancellations, the kids not wanting to meet you, and his ex being rude to you are fairly typical scenarios. Also, there might be days he or she doesn’t call or text you, and you might not be able to see the person as often as you’d like. Don’t be disappointed, it’s just the reality of dating after divorce.

13. If your date doesn’t call back, do not take it personally.

I know that sounds funny, because how can dating not be personal? The thing is, his or her reason for not calling could be about timing or personal issues and have nothing to do with you. He or she doesn’t know you well enough for it to be personal.

Dating after divorce can sometimes feel like an emotional roller coaster ride, with highs that seem heart stopping and promising, only to come barreling down by disappointment, rejection and frustration. But if you have the right mind set and the patience to put up with all the nightmare dates that precede him or her, the ride will be well worth it. Remember, you got out of a marriage that wasn’t working. This is the time to really get it right.

Jackie Pilossoph is the creator and editor-in-chief of Divorced Girl Smiling, a divorce support website for men and women. She is also the writer of Love Essentially, a weekly column published in the Chicago Tribune Pioneer Press, the LA Times, and several other newspapers across the country. Pilossoph holds a master's degree in journalism, and lives in Chicago with her two children.

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