Avoiding Tinder Swindlers When Dating in Midlife

dating single life Jul 13, 2022

It is a truth universally acknowledged that a woman in possession of significant assets must be wary of wolves.

Dating is always an adventure. Dating as an affluent, heterosexual midlife woman can sometimes feel more like white water rafting without the raft. Dirty John, The Tinder Swindler, and just about every Lifetime movie and Dateline episode provide cautionary tales of how dating can put your heart, security, and bank account at risk. And trust me, as someone who met the Devil’s uglier twin on one of those highly structured compatibility dating platforms, it’s smart to be cautious.

Here are some of the most popular dating options out there for midlife women, and how to keep yourself safe no matter what you encounter.

Online Dating in Midlife

Online dating is the most popular way of meeting someone, particularly after the last two years. Online can have its benefits since it’s like shopping on Net-a-Porter, only for men. Unlike Net-a-Porter, however, there is no quality control in place or assurance against fake goods. There are a whole lot of “CEOs” on there in the 50+ age range but it’s important to discern CEO of what. CEO of his basement? CEO of a Ponzi scheme? Buyer beware.

Tips: Many men online also see the site like online shopping. If someone ghosts you, don’t take it personally. Midlife men often choose to date much younger, in the beginning at least. And that’s cool. You have that option too. Just be aware that young, pretty things - male or female - who date older are often more transactional in nature. And that’s perfectly fine too. I’m not saying it’s going to be a full-blown sugar baby situation, but you are likely going to be paying for dinner given the economic imbalance. Decide what you want out of a dating situation. And be honest: don’t tell yourself you want a life partner when you really want a month with Magic Mike. Know your wants, set firm boundaries, and only meet in safe public places until you get a real read on someone. The best tip I ever received was to not spend too much time in chat, and to totally ignore those compatibility questionnaires because they allow sociopaths to appear human. Meet in person before you have any emotional investment and listen to your gut. Don’t let your brain talk you out of what your intuition is leading you to believe. If there are any red flags at all, believe them!

As for the Tinder Swindler of it all: if it seems too good to be true, it is. And everything - private jet flights, fancy cars, watches, clothes, apartments - can be rented for a day. The whole college admissions scandal showed us that charity work and athletic endeavors can easily be faked. Do your due diligence. If you are a well-heeled woman and think your online paramour may be '“the one,” you can always have a private investigator do a quick search. It’s also smart to let this person know that your assets are all tied up in trusts and foundations, your family office insists on marriage contracts, and that you plan to give away all your wealth à la MacKenzie Scott. it’s better to know early in the game if someone is simply after your wealth.

Meeting Cute in Midlife

If you are over 40, you were likely raised on Romantic Comedies and are well-versed in the concept of the meet-cute. Meeting someone as you reach for the same basket of strawberries or returning a piece of mis-delivered mail is considered more valid and authentic than swiping a certain way on an app.

Tips: Don’t let the way you meet change how you approach the relationship. Perhaps your meeting was a chance encounter that was “in the stars” or “meant to be.” Or it may be that predatory types often like to hang out in supermarkets manhandling the melons. Treat the person the same way you would as if you’d answered an ad on Craigslist. Know your wants, set boundaries, and look for red flags.


Sliding into DMs

I thought this was reserved for the young, but I’ve had guys slide into my DMs, particularly when I was spending some time on Clubhouse early in the pandemic. While I assume that the young, extremely good-looking, European jet-setters are bots, there were some real people and this is a genuine way people are meeting now.

Tips: If it’s too good to be true, it is. A lot of bitcoin and investment scams are being conducted through social media, so the person reaching out to you may be a professional getting a finder’s fee if you invest. If anyone you have just met wants to set you up with a too-good-to-be-true investment, run far far away. Also, understand that anything - and anyone - on social media can be face-tuned or fake. Have you ever ordered a dress from Instagram? What looks like a perfect dupe of the $2600 Oscar de la Renta dress you’ve been coveting shows up as a ball of scratchy polyester reeking of chemicals. It’s not worth $5, let alone the $79 they were charging. Assume the tech founder turned sensitive philanthropist reaching out via your DMS is the same. Again, get to know this person before assuming any good intentions. Meet for an IRL coffee at a safe spot in daylight.


Dating the Neighborhood Bachelor

I live in wealthy suburbia where the divorced end up dating other divorced people in their small social circle. It’s like that old show Wife Swap, only with more lawyers. I get it. There can be comfort in familiarity and knowing all of the same people can feel like a good thing. You also have referenced checked this person in advance, thus avoiding the risks of online dating. Plus, economically speaking, there is a better chance you get to stay in the same neighborhood if you are basically just swapping spouses.

Tips: Dating someone familiar may be comfortable, but it’s not a panacea. There is the saying that one woman’s trash is another woman’s treasure, but this is only true if said treasure has done a lot of inner work and healing. If you are about to get together with the newest single guy on the block, make sure he’s come to terms with his demons (I assume that if you are reading this, you are actively in the process of coming to terms with yours.) It’s easy to just slide into a comfortable relationship and continue to attend the same dinner parties, but is that really what you want? One of the biggest gifts of divorce is the opportunity to reinvent yourself and live a life that previously was not possible, but that will not happen if you stay in the same circles.

Matchmakers in Midlife

A lot of affluent midlife singles like the idea of a matchmaker since the vetting process adds a level of security. Matchmakers can work like executive recruiters, getting to know you and your needs and wants. The process of meeting with a matchmaker can really help you clarify what you are looking for in a relationship, which offers an added bonus.

Tips: There are matchmakers out there who are excellent and do what they claim. There are others who would happily introduce you to a serial killer for a fee. When I was at a post-divorce YOLO stage, I was set up by a matchmaker who was a friend of a friend. I was not paying a nickel, but, unbeknownst to me, my date was paying a hefty fee that increased if we stayed together for a certain period of time. It turns out there was some sort of Cyrano de Bergerac situation going on and my date was being coached in ways to woo me. Once the fees were no longer being paid, the intel stopped. My date was not nearly as appealing once his consigliere was no longer on the payroll. Any time there is an exchange of money, people tend to have an agenda. Make sure the matchmaker’s payment system is in alignment with your goals and that she or he is not coaching the client.

The Friend Set Up

I don’t know a soul who met their significant other through a friend set up but apparently, it does happen and it’s the ultimate in comfort dating.

Tips: Don’t take things personally. Once you’ve been on a few set-up dates, you’ll likely learn how little your besties know about you. That’s OK. Dating is a strange mix of taste and background and chemistry so it’s really hard to be an amateur matchmaker. If there is no love connection, be polite and friendly since your date is friends with someone you care for but do not feel any obligation to go out a second time. This is your life and romance so you don’t want to continue things simply to be polite. When I was young, I was set up by my friend to meet one of her good friends. He’d been fired that day, as it turned out, but felt obligated to go on the date. He was a terrible date: rude, caustic and bitter. I ended up sneaking out of the restaurant, aided by a sympathetic waitress, which make things a little awkward with my friend the next day until she’d heard my side of the story. Nobody should breach your boundaries so if the date is not going well, you have no obligation to salvage it. Your friend will understand.

Midlife Singles Events

There are hundreds of events set up for singles. I believe this is one of the better ways to meet since you rule out the whole online deception thing and your intuition has a chance to guide you out of the gate. You can go with friends, which can make you feel more comfortable and safer. It’s a low-stakes way to have a fun evening and maybe make a love connection. I went to a singles night at a museum after my first divorce. The men were kind of duds, but I heard an interesting lecture and had a night out. And I do know people who have met their partners at these events.


Tips: Singles events are like any other social event in the world. You’ll meet rude boors, close-talkers, and windbags, so it’s helpful to learn to bow out of an awkward conversation with grace. Keep the conversation light and airy. Don’t allow one person to dominate your time. Have a way to connect safely if someone is a keeper. Maybe have a card printed with a Gmail account you reserve for dating so you can easily disable the account if you read someone wrong and they become problematic. Talk to some of the other women at the event to get a feel for the room. I learned from one woman at the museum event that one guy ,who was aggressively circulating the room, attended this event regularly and would always tell people his profession was the same as the evening’s speaker. He’d be a political scientist one month and a marine biologist the next. Even grifters have a comfort zone, it seems.

Dating can and should be fun and dating in midlife can be particularly freeing. With more financial independence and no ticking of the biological clock, you can take your time to figure out exactly what you want. The key is to get yourself mentally healthy so that you are not looking for the relationship to fill a void (this was my big mistake after my first divorce.) If you are still dealing with wounds from divorce or bereavement, it’s important to meet with a therapist to help you process them before you get out in the dating world.

Know what you want, know your boundaries, trust your intuition, and have fun! If nothing else, you will have some interesting new stories to share with your friends. And if you'd like some help building midlife confidence, make sure you grab the free workbook