Dating Over 40? Here are the Red Flags You Should Watch For

Date - Drinking Wine - Woman Speaking on a Megaphone

When dating over 40, it can feel like an exhilarating, brand-new start. But it can also be tricky. While wisdom and knowledge often come with age, previous marriages, kids, and other baggage can further complicate things. When it comes to dating, it sometimes feels like you need to do a ton of research before getting your feet wet. It can be overwhelming, especially if you’ve been off the market for a while, so we’re here to help.

Here are a few red flags to watch out for if you’re over 40 and looking to find someone to date. From romantic swindlers to people who have never-ending drama with an ex, we’ve got the perfect tips to look out for.

1. They’re Unable to Handle Your Emotions

How you feel shouldn’t be up for debate. It’s normal to express your feelings. It’s also healthy as long as you take accountability for them and aren’t taking out your feelings on someone else. It’s a huge red flag if your partner can’t handle you discussing how you feel. If you try to tell them how you feel and they ask you to “tone down” your feelings or stop getting upset over nothing, they may not be your perfect match.

2. They’re Quick to Anger

You should move on quickly if you start seeing signs of an anger issue. It’s a big red flag if you’re dating someone with a short fuse who’s quick to anger. You don’t want a relationship when you feel like you’re walking around on eggshells, wondering what will set them off again. Plus, you don’t want to worry that you’ll be the focus of their anger the next time they get mad.

Instead, look for someone who can manage their frustrations and who doesn’t take them out on innocent people just because they’re around.

3. They’re Overly Sensitive or Defensive

By the same token, it’s a red flag if they’re always getting defensive when you ask a question. Are they unable to take any criticism or feedback without getting upset? In that case, they may not be emotionally mature enough to be in a healthy relationship.

When you date someone like this, they may leave you second-guessing yourself repeatedly. You’ll wind up always holding back on your true feelings for fear of saying or doing something to offend them. Instead, look for an individual who can listen to what you have to say without seeing it as a personal attack against them.

4. They Have Constant Drama with an Ex

After a certain age, saying someone has an ex sometimes seems bizarre. After all, the drama you dealt with in your teens, twenties, and thirties should be a thing of the past, right? You’re older, more mature, and know most of the dos and don’ts of dating—or so one would think. Surprisingly, the drama you had dating in your younger years can carry over well into your thirties, forties, and beyond.

While having ongoing drama with their ex doesn’t necessarily make them a bad person, these ongoing problems may make them unsuitable candidates for a long-term committed relationship with you—at least until they can get their situation resolved, or at the very least, minimalized.

Sometimes, people can’t help the drama, but even so, ultimately, they aren’t emotionally available when you need them because of all that’s going on in their lives. So what is considered drama with an ex? When you’re younger, relationship drama could mean not being over an ex or having an ex harass you.

Over 40, drama tends to involve “more mature” issues, such as being in a legal war over custody of the children or having just left a bad marriage and not being entirely divorced yet. If your partner has unfinished business that causes emotional chaos, you may need to rethink this relationship.

Questions to Ask if Your Partner Still Communicates with Their Ex

Should you be skeptical when someone tells you they’re still friends with their ex? Dating experts say yes. If your partner still speaks with their ex, ask these three questions.

1. Are You Secure in Your Relationship?

Feeling secure in a relationship is essential, but if you aren’t at that point yet, your significant other texting their ex might be a bigger issue than it needs to be. When a person feels insecure, it’s because their intuition is saying that something is off. When a person gets nervous about their partner’s communication with an ex, it’s likely a symptom of their insecurity rather than the cause. If you feel completely confident in your relationship with your partner, one or two texts here and there between your significant other and their ex isn’t going to change that.

That said, there is a difference between healthy and unhealthy communication with the ex, and most of it has to do with where your current relationship stands. So, if it’s inappropriate communication (ex, sexual in nature), discuss it with your partner and let them know you feel uncomfortable about the situation.

2. How Often Are Your Partner and Their Ex Talking?

What is your partner’s communication with their ex? You should know this because it’s important. Long story short, if it seems shifty, it likely is. You should be concerned about an ex when your partner gets secretive or defensive about their communication or the purpose of their conversations. If they’re in a healthy relationship with their ex, your SO should be willing to talk to them in your presence. You’d think that was obvious, but it is an essential distinction to make.

Bearded Man Texting

When your significant other mentions that their ex reached out to them in passing and gives up all the details, it’s less concerning than a partner who is constantly resetting their phone password or dodging your questions about their ex.

3. How Does Your Partner Act When You Mention or Ask about Their Ex?

Open communication with your partner is always a great idea and can be especially vital for touchy subjects like exes. Of course, this conversation can be challenging to approach, especially for those in a new relationship, because you want to be careful not to make unfounded accusations. Plus, you want to ensure that you give your new relationship enough time to determine the entire picture. Observe their communications over an extended period so that, if needed, you can present examples to your partner rather than just one incident.

5. They’re Always Trashing Their Ex

If you’re dating an individual who can’t stop trashing their ex, they probably haven’t healed from the relationship yet, so it may be best to pass on this one. An emotionally healthy person has processed their breakup or divorce and understands their hand in it. They are mature enough to know that often things don’t work out, and it’s not anyone’s fault. Of course, things might get slightly heated during the breakup or divorce process, but after time, everything should settle down.

Never let someone convince you that they’re the victim and it’s all someone else’s fault. There are two sides to every story, and a grown-up understands that. If they’re insistent that their ex is the only one to blame, if you break up, don’t be surprised if you’re the next scapegoat.

6. Their Kids’ Wants Always Come First

First, we need to distinguish between wants and needs. You should always meet your kids’ needs first before your partner. However, their wants shouldn’t be a priority. Unfortunately, some children don’t like to see their parents moving on and dating other people, so they’ll intentionally create disruptions. Of course, you want someone who takes care of their kids, but not someone who lets their children run their relationship.

Warning Signs of a Spoiled, Bratty Kid

It can begin as whining, but lately, you’ve noticed your partner’s kids acting more and more spoiled. Not sure if they’re headed for Bratty Town on a one-way ticket? Here are the warning signs of a spoiled child.

You Give In to Their Every Request.

You and your partner are tired today, so you’re not on your parenting A-game. Since you’re in no mood to deal with another tantrum, you give them whatever they want and will suffer the consequences later. Other times, you’re driven by your desire to provide them with everything you never had as a kid. It may seem harmless, but when you start spoiling a child, it only makes future parenting more difficult for you.

You Don’t Back Up Your Threats.

How many times have you threatened that if they do this behavior, you’ll punish them but never follow through? When you don’t back up your “promises” of punishment for bad behavior, the kids won’t have any repercussions for the misbehavior, so why should they listen to you?

Your Expectations Are Inconsistent.

Despite their demands, the child wants consistency with punishment and establishing expectations. For example, yesterday, you told the child to stop jumping on the couch, but today you let them roll around all over the floor with the couch cushions. Or, one day, you tell them to stop taking the cushions off the couch, and the next day you don’t say anything when they do it again. When you’re inconsistent, the kids aren’t sure what is and what isn’t allowed.

You’ve Never Taught Them Courtesy or Manners.

Manners and often be easily overlooked, especially if you’re inundated with monitoring your kid’s behavior. It can be challenging to remind them to say “please” and “thank you” when you can barely get them to eat their carrots at dinner. But teaching manners will save you a world of embarrassment. It also shows respect for another person, so you don’t want to skimp on teaching manners.

You Let Your Child Disrespect You.

We’ve all seen it: the kid who speaks disrespectfully to their mom as she attempts to help them with their homework., or the kid who terrorizes and insults their parents because, well, they can. It’s okay that kids get upset; we all do. But, as the parent, do not allow them to speak rudely to you. This teaches them to talk back to and disregard all adults.

They Have Too Much Input in Your Family Life.

Does your child decide you’re going to have dinner at their favorite restaurant again? While it’s okay to give them choices, your child’s options should be parent-approved. Sure, you can let them choose their outfit, but making the primary bedroom their new room is not the way to go. Feel free to allow them some input, but keep your child from taking control of family decisions.

You Block Your Child from Expressing Difficult Emotions.

No parent wants to see their child upset, but sometimes parents can take it a little too far. Some parents are so stuck on pleasing their kids that we attempt to shield them from disappointment. Or, we want them to be happy, so when we see them in pain, it hurts us. Often, we’d rather give in than allow them to have a meltdown or deal with their frustration.

To Get Things Done, You Have to Bribe Your Child.

Getting out of the house with your kids can be challenging for many parents. Kids often resist putting on their shoes, or they take forever to get dressed. It’s sometimes tempting to get them to do what you want with a bribe like: “Hurry up and get dressed, and we’ll get a toy at the store.” This usually happens when you’re exhausted from the struggle and want to move along. Unfortunately, kids are smart enough to realize that if they want something, all they have to do is make it difficult for mommy and daddy, and the cycle begins.

You Overindulge in Material Things.

Of course, we all want the best for our children, especially if we had terrible experiences growing up. Unfortunately, we overcompensate by giving them everything they want, from current trends their peers have to expensive vacations to places we never got to visit as children. But, when you take it too far, overindulgence is one telltale sign your child may be spoiled.

7. They’re Not Good with Children

On the other hand, if you have children, it’s essential to watch out for people who are rude or dismissive to them. It’s okay if they’re not kid people and don’t have any interest in having children of their own, but it’s a huge red flag if they don’t get along with your children, even just on a surface level.

Many people don’t have kids and don’t fully understand your parenting role, but they should be understanding and at least value family while supporting you. If they do have kids of their own and they still claim that they’re not a kid person, the alarm bell should sound like a four-alarm signal.

8. They’re Immediately Asking You for Financial Assistance

Over 40 daters, especially, should watch out for financially unstable people. At this stage of the game, your partner should have some assets to their name. Of course, people lose jobs, houses, and other financial securities due to divorce settlements and other unforeseen circumstances. Still, they should, at the very least, have a plan to get back on track, and that doesn’t include financial assistance from you.

Unfortunately, there are so many con people out there, so you should be wary if anyone asks you for money. Don’t give anyone money that you are only dating until you know them well enough and are in a long-term commitment to them. Otherwise, you stand to lose financial assets potentially.

9. They Become Easily Triggered

Does your partner go from 0 to 10 quickly? Are they constantly triggered by everything you say and do? It’s a big red flag if your date hasn’t been able to master their emotional life at this point in their life.

Dating over 40 means that you don’t need to worry about upsetting your significant other or bending over backward to keep the peace in the relationship. Part of growing up and being mature is developing some humility and being action-oriented when things don’t go as expected. This requires being able to ask, “What can I do to make the situation better?”

Man Discussing with Upset Partner

10. They Struggle with Being Sincere

They’re fun to be around, but if your date can ever stop being the comic relief and get sincere with you, you may feel like you don’t genuinely know them. While sincerity and humor are great qualities to help the ebb and flow of your relationship, deflection through humor can create a disconnect between you and your partner. When dating over 40, it’s reasonable to expect that your partner knows when it’s appropriate to crack a joke and when it’s time to get serious.

11. They Have Addiction Issues

Life can be challenging, and we all deal with anxiety in various ways. But if your partner consumes alcohol or takes drugs to unwind or have fun, you may want to run, not walk, in the other direction.

Addiction of any type is a red flag and shouldn’t be ignored. All addicts are unavailable emotionally because it’s part of the addiction pattern. Understand that it is not your responsibility to guide them out of their addiction. The best you can do is refer them to some professional help and wish them luck on their recovery journey.


By the age of 40, you should have worked out certain things in your life, including emotional maturity and financial stability. Of course, sometimes things in life happen and set you back, but at the very least, you should have a concrete plan in place and no longer be floundering around trying to decide what to do with your life.

So, if you witness any of these red flags in your partner, consider moving on because, after 40, you should not be dealing with unnecessary stress.

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