Eight Red Flags to Spot When You’re Dating


Debbie in a policeman's hat

Look! I’m the Dating Police

I’m an ex-online dating addict.  For a while, I was terribly social until I discovered binge-watching.  Here are seven red flags that cropped up when I was dating.  Sometimes, it took me weeks to figure out what the problem was.  But when he says these things, beware!

1.  Premature Commitment.  He says, “I see you in my spare room writing” or “I see you planning ny garden with me.” The problem: He barely knows you; he’s fantasizing you into the person he wants you to be.  Advice: Don’t agree to be exclusive prematurely or to act more interested  than you feel comfortable with. You don’t really know this person. They don’t know the real you,  just the lovely, fantasy woman they envision bringing light to their spare room.

2.  Discomfort over Widowhood.  He says:,”I’m worried that because you were widowed, you’re not really over your husband.” The problem:  This is presumptuous, implying we’re not ready to move on because we didn’t voluntarily end our marriages.  Each widow is different. Plus, if we’re dating, we’ve decided we’re ready. Advice: Reassure him once or twice that you are, indeed, ready to move on. If he persists with this concern, he’s probably insecure regardless of your widowhood.

3.  Lot’s of Dating Stories.  He says :”‘You must have some crazy dating stories.”  The Problem:  What he means, is that he has crazy dating stories he needs to share to reassure himself that he’s normal.   If you share too many stories, it looks like you’ve been “on the market” a long time. After awhile online, I started to feel like a cut-rate flounder.  Also, retelling old stories stops the conversation from moving on to what you both want now.  Advice:  Tell one story, listen to one of his.  Change the topic.

4.  He Falls out of Love.  He says, ” I fell out of love with my wife.  I deserve more.”  The problem:  If he’s been on his own for years and hasn’t been with anyone for a long period time, he may be incapable of sustaining love.  Also, didn’t his wife deserve more?  Marriages have their ups and downs, and I’m wary of someone who gives up because he “falls out of love.”  Advice: Gently ask questions to figure out more of his relationship history.

5.  Amazing Ex-girlfriend Dumped Him. He says,” My ex-girlfriend was gorgeous, but she left me.”  Or some other variant of things didn’t work out with the woman he was crazy about. The Problem:  He’s not over her, even if he thinks he is.  When I first started dating,  I went out with a smart Alec Baldwin lookalike who went on ad nauseam about his stunning, blonde, breast-enhanced ex.  It was torture.  Advice: Run.

6. Asks You to Pay Up. He says:  “Isn’t it your turn to get the check” or “Let’s split this.”  The problem:  It’s perfectly reasonable to share the costs of dating.  But, when he picks someplace pricey, then suggests splitting the tab, he’s being inconsiderate.  Similarly, when he asks you out,  but asks you to pay, it might mean he’s really cheap.  He should say ahead of time that he wants to split things.  You can too.

Advice: If you’re surprised by splitting or getting the tab, ask ahead the next time so you know what you’re paying for.  Plus, expecting you to pay for a place you didn’t choose (unless you already know you split everything), especially if it’s someplace expensive, indicates that he’s thoughtless in other areas as well. I speak from experience on this.

7.  Critical. He says,”I don’t think you’ll ever move, or change or buy the right brand of oatmeal.”  The problem:  I dated some guys who were critical when I didn’t know them well.  But, I hadn’t asked their opinions.  I was fine. They just wanted someone different.  This was their problem, not mine.  Advice: Call him on  it. Ask why he’s critiquing you.  If he persists after he knows you don’t like it, understand he won’t stop. That’s who he is.

8.  It’s All About Him. He says: “When I heard about your health problem or read about your husband’s death, it upset me.  I needed time to recover.”  The problem:  Everything is about how it affects HIM. Even if its something where he should be concerned for YOU.  Advice:  This fellow lacks empathy and he has no stamina for the vicissitudes of life.  Again, he’s not going to change. I dated one of these. Everything upset him and he needed ever so much coddling. Run.

Do any of these sound familiar? Let me know if there’s any flags I’ve missed.  Binge-watching is probably looking pretty good right now! 








  • Therese says:

    These are great tips and I will use them. Online dating is exhausting because it is so hard to find a man that is real and truthful. I just came out of a relationship with a man that I dated a year and thought I knew well. He lived on the east coast and I live in California, but we spent so much time together in 2016 and visited each other frequently. I was really attracted to who he was on the inside and his core values. We had a loving connection and his actions and words validated that. He was planning to move to California, as it was his dream and I was happy to help. Unfortunately, he was not as honest as I thought. He announced without warning that he was not that in to me. We had just bought 2 plane tickets for the holidays two days earlier. I was stunned, but in retrospect I ignored many signs. He was not legally divorced (was working on it), had a long loveless marriage (mostly his wife’s fault), plus many other red flags. I am actually relieved, as everything works out for a reason. I was spared a lot of future pain. I believe he is a good person, but not emotionally available. I am adding that to my requirement list as well. I have not given up yet.:)

    Thank you for the great articles. I always look forward to reading them.

    • Debbie says:

      Thanks Therese! And thank you for sharing your story. I think it will help other people. There is a red flag for people who are not yet fully divorced and/or have not emotionally processed their divorces. I also have problems when a guy complains a lot about his ex-wife. He may still be angry or processing. I’m glad you’re okay following the break up and see it so positively!

  • Debbie G says:

    I really appreciate whenever you share your online dating experiences and what you have learned. I’m not a very assertive person when it comes to online dating, so it’s slow going for me, which is fine. I’m also appreciating Netflix in a big way!

    • Debbie says:

      Thank you! And I think slow-going may be the way to go in online land. Otherwise it’s a big time waste. If you have Amazon Prime, there are some great series to try! 😉

  • Ted says:

    From the other side, one guy’s perspective on two years of online dating (with hat tip to Harper’s Index).

    Number of woman on first date said they had a “great time” and it “was really fun” whose next contact was a text or email message stating, “This is just not the right time for me to date.” 4

    Number of woman met face-to-face from online contacts: 11. That led to “dates” of an activity other than meeting for coffee or drink: 6. Number of women who admitted to lying about their age: 4. Number who lied about their status: 1.

    Dollars expended on online dating sites in two years: $250. Approximate cost of dinners, drinks or excursions/concerts with dates: $600 (guess).

    Length of second-longest relationship garnered through online site: One month. Cause of breakup: She felt it wasn’t a good time to date and wanted to focus on her son, a sophomore in high school.

    Length of longest relationship garnered through online site: Six months. Cause of breakup: She wanted to explore singlehood, which she didn’t have in her 20s. Wanted “to be 25 and single for once in my life.”

    My response: Shrug.

    Number of friendships gained through online dating: One.

    • Debbie says:

      This is brilliant. So, it sounds like women who date online may tend to be uncertain about what they want. I guess lot’s of people lie abut their age…I certainly met men who did. Oh the vanity!