THE BLOG
06/20/2013 05:03 pm ET Updated Aug 20, 2013

Dating After Divorce: What Not To Do on a First Date

I'm not sure I've ever met anyone who really enjoys first dates. First dates, especially when it pertains to dating after divorce can be awkward, uncomfortable, boring, weird, or just plain awful.

"Do I have food in my teeth?" "Is this guy really interested in anything I'm saying?" "Is he cute? I can't decide." "Does she seem a little too bitter about her ex-husband?" "Does he think I'm fat?" "Was he disappointed when he came to the door?" "Does this girl like me?" These are some of the questions going through the minds of men and women on first dates.

If you want to increase your changes of success on a first date, here are five things not to do. They might make the difference when it comes to making plans for date number two versus experiencing a first date flop.

1. Don't eat like a bird. This is all part of being yourself. If you like to eat and/or if you are hungry, just eat. If you pick at your food, one of three things will happen. One, your date will think you don't like the meal, two, he or she will feel uncomfortable because they are eating and you're not, or three, you will be perceived as having an eating disorder.

2. Don't keep checking your iPhone. Put the thing in your purse and keep it there. If this person is investing his or her time to go out for dinner with you, he or she deserves your full attention. You can text your friends when you get home. Exception: If you have kids, and you have a new babysitter, you can keep the phone out, but tell your date that's the reason it's out.

3. Don't pay for dinner. This is for women. Make the guy feel like the guy by paying. If you offer to pay the first time you go out, he will probably be disappointed and feel less manly. My rule of thumb is offer (insist, actually) on paying on the fourth date, (or make him dinner for the fourth date.) I do think it's okay to pay for a Coke for him if you go to a movie afterwards, or pay for a round of drinks if you go to a bar. That's just a nice gesture.

4. Don't talk about your last relationship, OR your ex. Trust me on this one. He or she might ask you about your divorce, and it's okay to give a brief, not too emotional summation of what happened, but stop there. Trust me! Don't say, "He's a jerk," or "she's psychotic" or "I hope he burns in hell," and don't provide details about cheating, fighting and all of your ex's faults. If you do, you will have this person running away so fast your head will spin.

5. Don't have sex. A friend of mine would completely disagree and say that I'm living in the 50s, but the reason I feel this way isn't just because the guy will think you're easy. He might not even think that. These days, it seems like sex on a first date isn't that big of a deal, which makes me sad in a way. Here's my reasoning behind saving the sex for down the road. I think it's a good thing to let the new relationship breathe. Get to know each other and let the attraction build. Kissing is fun and sexy, so just do that. If you wait just a little while, it will be so much better and will mean more.

First Date Red Flags: If he or she does any of these, dump the person fast!

1. If he or she orders several cocktails (more than three) on the date, dump him or her!
2. If he or she keeps checking their iPhone, dump him or her!
3. For women: If he starts talking dirty, alluding to how great the sex with you is going to be, dump him!
4. For women: If he gets the bill and questions the waiter about something on it, or thinks the amount is incorrect, dump him! Guys, you can't really worry about the check being perfectly correct on a first date. You just can't.

Jackie Pilossoph is the author of the blog, Divorced Girl Smiling. She is also the author of the comedic novel, FREE GIFT WITH PURCHASE, about life after divorce. Ms. Pilossoph is a weekly business features reporter for the Pioneer Press, with the monthly column, "Heart of the North Shore." She lives in Chicago with her two kids. And she's divorced (obviously.)

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