Hitting the dating scene in your fifth decade can feel so… complicated. After all, there are likely to be children in the picture, and behind every potential partner is a sheer lifetime of romantic experience (and a much, much longer trail of exes). But we’d argue that none of this is a bad thing. In fact, if you’re dating as a forty-something, you’re guaranteed to be wiser, better at dating, better at knowing what you want, and a lot less impulsive and sensitive to rejection.
That said, if you’re recently single for the first time in a long time, you may not know where to begin. So we tapped dating experts and compiled the very best dating tips for women on the cusp of middle age, which you’ll find right here. (And if you happen to live in any of The 50 Cities with the Best Dating Scenes, these rules are especially applicable.)
Be realistic. “And remember the rule of thumb: Bad dates are one step closer to a good one,” says Stef Safran, a matchmaking and dating expert and owner of Stef and The City. If it’s a first date, though, make sure you don’t ask any of the 20 Questions You Should Never Ask On A First Date.
Especially since they might be different from when you were in your 20s and 30s. “When you know what you won’t tolerate, it’s easier to date smart,” says April Masini, a New-York-based relationship and etiquette expert. “For instance, if you don’t want to date someone who has kids, you’ll save yourself loads of time by simply saying no to anyone who wants to date you and who already has a brood. Same goes for money, religion, and lifestyle. Forget judgment—just be true to you and you’ll be successful at dating.”
It’s just poor form in the beginning stages of a relationship. “It’s a big turn-off and it shows you haven’t moved beyond that relationship,” says Elliott Katz, author of Being the Strong Man a Woman Wants: Timeless Wisdom on Being a Man. “The man you are dating may have an ex-spouse who already badmouths him; he’s not looking for another.” And for more essential dating advice, don’t miss the 20 Signs He’s Going to Ghost You.
“Sure, we may all have had a ‘type’ that attracted us in the past, but to find a quality partner, it’s time to grow up,” says Laney Zukerman, a relationship coach and author. “There are many potential partners out there that are diamonds in the rough. It’s not always easy, but think outside the box.”
“A lot of women who have been dating for a long time arrive to the date with certain assumptions because a man ‘seems’ like someone else they’ve gone out with,” explains Samantha Daniels, relationship expert and founder of The Dating Lounge dating app. “Try to just get to know the man in front of you instead of comparing him to men in your past.”
“Just because there are younger women available does not mean that a man will choose one,” notes Megan Weks, dating and relationship expert. “You get what you expect in life, so if you’re out there deciding for him, you will show up as less desirable based on your inner beliefs.”
“Too often women over 40 rush back into dating because they are accustomed to being in a relationship,” says Monte Drenner, a licensed counselor and consultant. “They feel like they need one or they are pushed into the dating scene prematurely by well-meaning friends or family. I always encourage clients to make sure they have healed from the wounds of previous relationships prior to pursuing another one.”
“If you are overweight, have some wrinkles, whatever, don’t post a photo online of you 20 years ago,” advises Jane Coloccia, author of Confessions Of An Online Dating Addict. “A guy is going to show up to a first date expecting to see that girl—not the woman you are today. Just accept yourself and be okay with who you are now. When you own who you are now, you’ll be in a much better place to be in a truthful, honest, open relationship.”
“Dating can require a tough skin. Start developing one now,” recommends Renée Suzanne, a dating coach. “Nothing that a stranger does online is really about you. Having a fulfilling love life is worth enduring a few setbacks. Hang in there!”
“The most important thing a women over 40 can do to increase her chances of meeting a great guy is to initiate contact with a shy guy,” says Richard Gosse, author of The Donald Trump Syndrome: Why Women Choose the Wrong Men to Love. “Forty percent of the American population is shy,” according to Dr. Phillip Zimbardo, Director of The Shyness Institute at Stanford University. “That’s millions of guys who seldom meet women because they are too shy. There’s very little competition for these bachelors—and you can have your pick, if you are willing to make the first move.”
“Usually, the more couples have in common on core areas of life the more likely they’ll have a successful relationship,” says Dr. Wyatt Fisher, a licensed psychologist in Denver, CO. “Therefore, spend time finding someone similar to yourself.”
“Many women are looking for a ‘good’ partner but have not defined what good looks like,” Drenner explains. “The more clearly ‘good’ is defined, the sooner your will be able to eliminate those that don’t fit the criteria.”
“It’s very easy to fall back on humor when you’re nervous, but you need to make sure that it’s not at your expense,” says Laura Bilotta, a dating coach and matchmaker in Toronto. “Even if you are genuinely joking, your date may perceive you to be very negative and lacking self-confidence.”
“You don’t have to grace the cover of Vogue, but you do have to strive to be your best, unique self,” Masini says. That means exercising, eating well, and taking up grooming habits you enjoy—like regular mani-pedis, if that’s your thing.
“Seeing how someone interacts with his friends and his family will tell you a lot about who he is as a person,” says Monique Honaman, author and relationship expert. “With so many dating scams out there and people pretending to be who they are not, this is a great way to see for yourself that the person you are dating is authentic.”
“Everyone makes mistakes. It’s acknowledging your mistakes and showing that you learned from them and are a better potential partner for it that will make you attractive,” Katz notes.
“You may have a great body, but your attempt to show that you are incredibly hot in your 40’s is not the best way to be taken seriously,” says Rhonda Milrad, LCSW, relationship therapist and founder of online relationship community, Relationup. “Your date will be objectifying you before even meeting you, and thinking about getting you naked rather than getting to know you.”
There’s nothing wrong with being single in your 40s, so no need to act like there is! “Keep in mind that the man across the table from you is ‘still single,’ as well, so don’t be embarrassed or uncomfortable about your own dating status,” Daniels suggests.
“If you were catching birds would you place your bird seed in multiple places or would you have it in just one place? Your odds of meeting someone increase when you are more visible, so take a risk and put yourself out there,” Weks advises.
It doesn’t have to be luxe to be fun. “Dating is expensive for both parties and men also want to make sure that the person that they like is going to stick around past the first few dates,” Safran says.
Chances are, love won’t just fall into your lap. “Singles hate this advice because they want the universe to provide,” Gosse says, but this standard dating guidance really is true.
“Women over 40 sometimes convince themselves that there are not many good opportunities for a future mate on the dating scene after 40, and therefore settle for the first good candidate who comes along,” Drenner says. “Too often, they make the ‘smart choice,’ meaning a good potential partner that cares for them, rather than the ‘heart choice,’ who is someone they love.” So go ahead and hold out for someone who you really, truly love.
“If you’re meeting someone online, be sure to spend several weeks getting to know them online first through emails and video chats,” suggests Fisher. “It’s also recommended to do a background check to ensure they have no criminal background and aren’t already married. If all checks out, be sure to keep your first few dates in public and bring your own mode of transportation to maximize your safety.”
“I know that a man who is 55 or older might seem like your father, but he is actually your contemporary now—especially in the dating world,” Daniels says. “Age is just a number, so give him a chance.”
“If you have kids, don’t make your life and your conversations all about the kids. Men want to know you have a life outside of your kids, which will hopefully include them,” Coloccia says.
“Choosing another potential mate can be an extremely difficult process. I recommend that women form a ‘committee’ of trusted advisers to help them to navigate all of the difficulties of the process of finding another mate,” Drenner says. “These committee members can help identify areas of concern and help to prevent mistakes.” In other words, go ahead and ask your friends and family what they think of your new potential partners, and encourage them to be honest.
“Frequently when dating past 40, different scenarios come into play such as co-parenting and step-parenting relationships,” Honaman points out. “This may require flexibility as you work around ‘I have the kids this weekend’ or go on ‘dates’ with children involved. I’ve found some women get frustrated with the ‘I have the kids this weekend’ scenario because it can dampen their spontaneity and they lose that one-on-one time that’s so important when dating, but it also might mean that the following weekend is a ‘child-free’ weekend.”
“So many women (and some men) think they know their boundaries and yet accept unreasonable demands when they think they meet ‘the one,’” Zuckerman explains. “If you are accepting the unacceptable, over time it is a recipe for disaster! Know what you will and won’t tolerate in a partner and no matter what, hold your ground.”
“Lots of people who are married but living as single fool themselves and others into thinking they’re legally single,” Masini says. “When it’s found out that they aren’t, all hell breaks loose and allegations of lying and cheating are flung about. Remember, if you’re married but separated, you’re married. If you’re married and living single, you’re married. If you want to date married, at least be honest with yourself and those you’re dating. But best of all, if you want to be single, make sure you are—legally.”
“If you think that love should ‘just happen’ or it’s not meant to be, it’s time to rethink your dating plan,” Suzanne says. “Think about it, you’ve gotten where you are in life by taking action, not waiting for the fates to drop the things you want on your doorstep.”
Generally, it’s a good idea to project that you’re self-sufficient when dating older men. “The man you are dating may have children he is supporting,” Katz points out. “He’s probably not looking for another dependent.”
Seriously. “David Ian Perrett, an expert in the science of human attraction, found that men consistently rate photos of women taken by a man as more attractive than photos taken by a woman,” says Scott Valdez, founder of ViDA. “So if you’re investing in pro photos for your dating profiles, book a male photographer, and if you’re taking casual snaps with friends, hand your phone to one of the guys.”
Save it for later dates. “Your ex or a custody battle may be a large part of your life, but it’s probably best to not let it control your conversation on your first few dates,” Bilotta says. “You want your date to learn about you and what makes you great, and you want to find out about them.”
“For most women over 40, the dating scene has changed a great deal since they were in it last. The majority of women I counsel underestimate the time, effort and energy it takes to find someone they really desire to be with,” Drenner says. “If they are prepared for a long process, they are more likely to keep persevering rather than settling or quitting.”
“Take some time to be alone, be comfortable being alone and with yourself, and decide what it is that you really want out of your next relationship,” suggests Coloccia. “By getting clear about who you are and what you want, the right person will show up.”
“Stay positive and surround yourself with people who have a positive outlook and who believe in love,” Weks recommends. “Negativity is contagious, and it’s the very last thing you need around you when dating.”
“A lot of people end up in dating ruts by going to the same places and seeing the same friends all the time,” Daniels says. “Try new places, reach out to other friends for setups, or try a new dating app and see if that can help you meet some new men.”
You might think they’re for 18-year-olds, but in reality, they’re pretty great for people of all ages. “Tinder and Bumble are fantastic because you need to express interest in someone before they can contact you,” Suzanne explains. “This means you won’t have an inbox full of messages from men you’d never want to meet. These apps aren’t just for hookups. Real couples meet on them every day.”
“Make sure you keep your options open until you know that this man wants what you want and wants it on a similar timeline,” Weks says.
If things just don’t seem to be going your way on the dating scene, don’t hesitate to recruit a professional. “Ask an expert, spend time doing activities you love without worrying about meeting someone, take a break, and put new pictures up every three months,” Safran advises. “Remember that it’s okay to need a break and it’s okay if you need help.”
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