What Red Flags Should a 20-something Look for in Dating?

Q. Dear 40-somethings: What are big red flags 20-somethings should be aware of when dating? – 20-something


A. Dear 20-something:

Red flags…may all be in the eye of the beholder but there are some common themes in the answers received…and there were a lot of responses! In the end, as one women pointed out, it comes back to that the biggest red flag is you. If you are asking about red flags, are you feeling something is missing. Then ask yourself why? We also have a contrarian view…that perhaps there is so much media about what to watch out for that we are looking for flags instead of being present in the relationship. Which goes back to questioning how fulfilled you are in many ways.

Here are the perspectives:

1. The Mom Factor

“I think the biggest red flags are, 1) the guy doesn’t have any close male friends or does anything social on his own.  2) He either doesn’t get along with his mother or speaks to her TOO much!” –  40-something, musician, broker, NYC

2. Friends and Family Relationships

Another good indicator of intimacy potential is one’s relationship with family and friends. This is a common them I have noticed.  One woman observed, “It’s easy to be nice and courteous on the first couple of dates when you’re trying to make a good impression. It’s how he treats others, his family and friends, that will shed light on what is in store for you.”

Even relationships with a random strangers, waiters and service people can be a sign of one’s true nature. How does he interact when he is not trying to impress?

“I think a huge red flag is when a man isn’t kind or generous with others. Even if he treats you well now, he will likely change at some point! Pay close attention to how he talks with waiters for example. Just my two cents worth!” – reader submission

One caution I add here is that it should not be just a crossing off the list of “Oh, he comes from a divorced family or doesn’t talk to x family member.” Take the time to understand the relationship dynamic (e.g. was he the source of family discord or the victim”) rather than rush to snap judgment. One woman I interviewed with crossed a guy she dated and truly connected with off her list because he came from a dysfunctional family and she was determined that she didn’t want the same (and was very certain she wanted a family). They ended up back together some years later after she had gone through some soul searching of her own. She found she was projecting her own issues. They are now happily married with two kids and he’s a great father.

 3. Self Esteem

“A big red flag is low self-esteem. It is the underlying problem of low motivation, social awkwardness, destructive behavior and substance abuse.  All of those issues are difficult to deal with in a partner.   My best advice is to look for someone you have things in common with, particularly morals, education level and sense of humor.  These traits are often reflective of how a person will evolve.  Lastly, if there is no chemistry or attraction, move on. – 40-something, fashion designer, business owner, Brooklyn, NY

4. Follow Through / Making Excuses for Him

Does he take more than he gives based on what YOU are looking for and needing in a relationship?  And that means following through on what he promises to give to the relationship rather than continuously dangling the carrot of commitment.

“It all depends on what you are looking for.  If you want a committed relationship, then your partner’s ability and willingness to be present and follow through is critical.  Always listen to your gut and when you find yourself justifying his/her actions and making excuses for him/her, then you need to reassess.  The key red flags should be your own actions/reactions; if you start compromising yourself and what you really want in an effort to please/keep someone else, then something is very wrong. – 40-something, financial advisor, NYC

The making excuses part extends to his commitment to see your friends or family (after time) as well. If he is constantly wriggling out of being part of your social commitments take a look. One woman added that the ability to sacrifice (e.g. give up the golf game to attend a family event) needs to be present before you commit to a long-term partnership.

5. How He Makes Excuses

Perhaps having to give excuses is a red flag as this woman notes. You don’t want to feel as if you are in a constantly in search of the truth.

“Feeling that all the true facts provided as part of his excuses don’t mean the truth: When you feel that the only way you’ll get the truth is if he is in court and being cross-examined by a savvy attorney.” – reader submission.

This reminds me of a conversation a man and woman (good friends) shared about being with a manipulative partner. The woman was questioning her boyfriend’s behavior. The man shared that a certain type of guy will try to take the blame off themselves by pointing it toward the accuser/ questioner. He called this the “lie, deny and counter-accuse” tactic.

6. Too Good to Be True

If he says all the right things, but not at the right time, then he is likely trying to move something forward but not necessarily a commitment says this woman. Beware of sweet nothings too soon:

“Artificially accelerating the relationship. For example he says, “I always wanted a father-in-law who enjoys fishing” on your second date in response to sharing the general family chit-chat of first date conversation.”

I have heard this from the “guy’s eye view” as well. Watch out for the guy who approaches you and then comes on as incredibly romantic and over the top.  They often have their own self-interest in mind.

This is different from the guy who you have a first date with and end up having a natural and interesting conversation. One of the biggest green lights I hear is from couples who say their first date was so easy…they could have stayed up all night talking.

7. The Guys’  Eye View

And speaking of guys…one former player and observer lists:

– He won’t give up guys’ night…ever.

– When other girls come up to him and are hugging him and openly affectionate in front of you and he tells you it’s not a big deal.

– He turns the table to makes you feel bad (re: the above, saying things such as, “Why are you making such a big deal out of it? You are so insecure? This is boring.”

– And of course, if he says he is not looking for a relationship, believe him!

7. You

“If you are early on in a relationship and you are looking for red flags, look at yourself. Are you happy in the relationship? Probably not. If you are asking yourself are red flags… You already know the answer. Yes there are. And you are not happy so the flags are within you.  Are you satisfied? Is the person giving you what you want? Is the person caring about you? If the answer is no no no, then don’t make it about the other person, make it about you. Are you happy?”

8. Spending Too Much Time Looking for Red Flags

“There is so much written in magazines and online about relationships I think it makes it easy to doubt your relationships. Women tend to compare all the time as well…so that creates this tendency to look for the negatives in your relationship. Are you taking cures from negative people? Try to be present in your own relationship and pay attention to what makes you fulfilled. The worst thing you can do is to judge your relationship on other people’s opinions.”

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