5 Red Flags to Look Out for When Dating Over 40, According to a Matchmaker

Dating over 40 can feel like an exciting fresh start, but it can also be tricky. There are often previous marriages and/or kids involved, and though knowledge and wisdom come with age, so too does baggage and wariness. “When it comes to dating, sometimes it sure does seem like you need to read volumes before getting back out there and taking the plunge,” matchmaker Susan Trombetti, tells us. “It's overwhelming especially if you haven't dated for a while.” That’s why we asked Trombetti for five red flags to look out for if you’re dating over 40, from romantic scammers to people who have ongoing drama with their ex.

Meet the Expert

Susan Trombetti is a matchmaker and CEO of Exclusive Matchmaking, a company that helps singles discover long-term happiness.

3 Red Flags to Look Out for on Your First 3 Dates with Someone New

older couple on a date
Janie Airey/getty images

1. They Have Ongoing Drama with an Ex

Trombetti says that while this might not make them a bad person, these ongoing issues make them unsuitable for a relationship with you until they can get things resolved, or at least minimized. “They can't help some drama…but they aren't completely emotionally available to you when so much else is going on in their life,” she says. This could mean they’re in a legal war over custody, or they’re coming off a bad marriage and aren't divorced yet. “If they have unfinished business that creates emotional turmoil, you may need to give this relationship a pass.”

2. They Always Put Their Kids’ Wants Before Your Relationship Needs

First, let’s distinguish between wants and needs. “Your kids’ needs should always come first before your significant other, but their wants shouldn't,” Trombetti says, adding that some kids don't like to see their parents dating and will intentionally create distractions. She tells us that you want someone that takes care of their kids, of course, but not someone who allows their kids to run your relationship.

3. They’re Not Good with Kids

On the flip side, Trombetti says that if you have kids, it’s important to be on the lookout for people that are dismissive of or rude to your kids. It’s OK if they’re not kid people and have no interest in having kids of their own, but it’s a major red flag if they can’t get along with your kids, even just on a surface level. She explains, “It's OK for them not to have kids and not understand exactly what your parenting role is, but they need to be understanding and value family while supporting you.” If they do have children of their own and they still proclaim not to be a kid person, alarm bells should be going off.

4. They Constantly Trash Their Ex

If you’re dating someone who can stop trashing their ex, they likely haven't healed yet, and it might best to take a pass. “An emotionally healthy person has processed the divorce or breakup, and understands their part in it,” Trombetti says. “They are grown up enough to know that sometimes things don't work out, and it's no one's fault.” Of course, things might become a little heated during the divorce or breakup process, but everything should settle down after a while. “Don't let someone convince you that they are a victim. Move on.”

5. They Ask You for Financial Help Right Off the Bat

Older daters especially should be on the lookout for financial grifters and romantic scammers. “There are so many financial cons out there, so you need to beware anyone that asks for money,” Trombetti warns. “Do not give anyone money that you are just dating until you know them well and are in a long-established relationship.”

sarah stiefvater

Wellness Director

Sarah Stiefvater is PureWow's Wellness Director. She's been at PureWow for ten years, and in that time has written and edited stories across all categories, but currently focuses...