Ten Dating Red Flags

You are ready to get out there and start dating again. You are both excited about the possibilities and terrified that you will find a loser. Chances are you will meet some wonderful - and not so wonderful - men during your journey. Your responsibility is to know exactly what you want in a man and to keep your eyes open for potential red flags.

 Dating Red Flag #1 - Is He Wealthy?

He spends money frivolously and likes to flash wads of money. He drives an expensive, fast fancy car, wears a rolodex and expensive jewelry, clothing and other accessories. He lavishes you at the finest of restaurant and is always bragging about how much money he has.

Questions to ask yourself:

  • What does he do for a living?
  • Does he own his home?
  • Could he be pretending he is wealthy to impress you?

 Dating Red Flag #2 - Is He Broke?

He conveniently disappears when the check arrives and leaves you to pay it. He never offers to pay for anything. Everywhere he takes you is somewhere free. He expects you to drive and never offers to pay for gas. He tends to pop-up at your house every evening for dinner.

Questions to ask yourself:

  • Does he work?
  • Where is he living?
  • Is he just a cheapskate?

 Dating Red Flag #3 - What Does He Do?

You have been dating for a month or two and he has yet to articulate what he does for a living. He appears nice enough, but conveniently avoids answering personal questions about himself. He may say things like, “I am a jack of all trades,” “I make money in a variety of ways” or “It’s complicated.”

Questions to ask yourself:

  • What is he hiding?
  • Is he married?
  • Is he doing something illegal?

 Dating Red Flag #4 - How Many Mamas’?

Your dating someone a little older. He admits to having several children with various women.

Questions to ask yourself:

  • Were the mama’s pregnant at the same time?
  • Is he actively involved in the children’s lives?
  • Are you willing to put up with the drama? (especially if there are young children involved.)

Dating Red Flag #5 - Where Does He Live?

You just find out the man you have been dating is living with his mom or in his sister’s basement. Another scenario could be that he crashes with various friends or lives with a couple of women.

Questions to ask yourself:

  • What are the circumstances?
  • How long has he been living like this?
  • Does he have a solid plan to venture out on his own?

 Dating Red Flag #6 - He Said What?

Everything that comes out of his mouth has a negative aura about it. He complains about his job, the economy, his childhood, his friends, his health and anything else you can think of. He never has anything good to say and bad mouths others consistently.

Questions to ask yourself:

  • What are you waiting for? Run for the hills!!!
  • Why are you allowing his negativity to bring you down?
  • Do you feel sorry for him and want to “fix” his life?

 Dating Red Flag #7- What Does He Tell You?

He tells you to wear his favorite color or certain types of clothing when going out on a date (or he buys your clothes to wear.) He tells you how and when to do everything. He tells you that you are doing it the wrong way or that things you are interested in are stupid.

Questions to ask yourself:

  • Does he get extremely angry if you do not follow through?
  • Does he ever apologize to you?
  • Do you really want to be controlled by another person?

 Dating Red Flag #8 - Is He Jealous?

He tells you that he sees you looking at other men. He does not like you talking to other men - including your friend’s husbands or your brother’s friends. He says that he wants you all to himself and does not like to share. He may also be jealous of the time you spend with your family, friends or children.

Questions to ask yourself:

  • Does he have a reason to be jealous?
  • Does his jealousy control where and when you go out?
  • What are you waiting for? Run for the hills!!!

 Dating Red Flag #9 - He Won’t What?

You have made plans for him to meet your family or friends a few times. At the last minute he always cancels because “something came up.” He gives you hundreds of excuses as to why he is afraid to meet them or cannot meet them.

Questions to ask yourself:

  • Is he afraid they will not like him (or see his true colors?)
  • Is he trying to control you by alienating you from family and friends?
  • How many more chances are you willing to give him?

Dating Red Flag #10 - What Did They Say?

He has met your family and friends and none of them have anything good to say about him. It is important to remember that they love you and truly want you to be happy. There is no need to be concerned if only one or two people have something bad to say … but if everyone is saying it …

Questions to ask yourself:

  • What are they seeing - and what should I look out for?
  • Are they all saying the same thing?
  • Do I trust my family and friends?

Just about any situation can be viewed as a dating red flag, based on your previous experiences with your ex-husband. Consider everything and make a list of what you will and will not tolerate in a relationship along with red flags that could point to him being like your ex. After all you do not want to wind up with another man that is exactly like your ex, just with a different name and body. Most of all trust in yourself and trust your intuition!


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Filed Under: Dating, Life After Divorce


  1. I appreciated the 10 Red Flags since I have seen many of them while trying to navigate through the rugged terrain of dating after my 20 yr marriage destructed like a tsunami.
    What about guys who say they are ready for a relationship, but really aren’t due to not enough time following their divorces or their emotional blocks and inability to get their feelings out and dealt with following their divorce or loss of spouse?
    I’ve ended up getting in dating relationships with guys like this and have ended up getting very hurt as they abruptly press the EJECT button about 3-4 months into dating them!

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