How to Woo an Older Woman: 18 Tips for Winning Her Over

Whether you’re crushing on a woman only somewhat older than you or you’re in your Harold & Maude era (respect!), the prospect of trying to attract an older woman might seem intimidating, but it’s honestly pretty simple. Older women tend to know what they want, which makes it easier for you to know what they want. We’ve created a guide for wooing the older woman of your dreams, from attracting her attention to striking up a relationship, including expert tips from dating coaches Imad Jbara and John Keegan, as well as licensed relationship psychologist Jessica January Behr, PsyD.

How to Attract an Older Woman

Ask her questions about herself and take an interest in her hobbies.
Take her out someplace you can get to know her better, like dinner, but be fun and spontaneous—for instance, by taking her for ice cream afterward.
Avoid taking the age difference to heart. If she’s the right person for you and you’re both consenting adults, age doesn’t matter.

Section 1 of 6:

Getting to Know Her

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If your flirtation is in the early stages, simply exchange a smile. Tell her how pretty she looks today, or compliment her on her outfit. Speak specifically about her as a person, about her laugh, her eyes, and any unique mannerisms you pick up on. Limit physical contact to light arm grazes or handshakes, especially at first. Look her in the eye when you’re speaking to her to show your attention is fully on her.

Meet the wikiHow Experts

Imad Jbara is a dating coach for NYC Wingwoman LLC, a relationship coaching service based in New York City. He specializes in authentic communication skills.

Jessica January Behr, PsyD is a Licensed Clinical Psychologist and the Founder and Director of Behr Psychology. She specializes in couples and sex therapy.

John Keegan is a Dating Coach and motivational speaker based in New York City with over 15 years of professional experience.
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Approach her confidently. Stand up straight, don't slouch, and keep a smile on your face. And believe in yourself: never think that you don't deserve to date the woman of your dreams . Think positively about your prospects—older women detect that level of confidence and are attracted to it. Speak smoothly, and crack a joke every once in a while to get her to laugh. ^{[1]
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- Keep the conversation going. Ask her questions and tell funny anecdotes.
- Being confident isn’t the same thing as being cocky. Know your worth, but don’t be entitled, boastful, or arrogant.
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Don’t focus on age. If you suspect there is a significant age gap, she’ll probably suspect it too. When she inevitably asks you how old you are, try to playfully dodge the question the first time. While we are not at all suggesting that you be dishonest, Jbara advises that you answer the question with humor and charm: “Make a joke like, ‘Old enough to be an awesome guy.’ That creates the mystery.” He adds that when she actually gets to know you for who you are, the truth about your age won’t matter too much. ^{[2]
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Imad Jbara
Dating Coach

Expert Interview}
- Jbara explains that once she can actually “make an accurate judgment of your character based on who you are as an individual, then it's okay to tell her your age.” ^{[3]
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  Imad Jbara
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- If she asks seriously, be honest about your age, but don’t make it a big point of conversation.
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Show interest in her as a person. Ask her questions about herself: where she works, what sports she plays, what college she goes to or went to, and where her family is from. These are questions that show that you sincerely care about getting to know her as a person. Since she is more mature and has more life experiences, you can try asking her questions like:
- What’s your favorite place you’ve ever traveled to?
- What 3 songs would be featured on the soundtrack of your life?
- What do you do to cheer yourself up when you’re feeling down?
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Adopt some of her hobbies to spend time with her. If she likes to volunteer at the food bank, for example, signing up yourself will allow you to get to know her better and maybe even get her to notice you. This especially works when she knows that the given activity is out of your comfort zone. For example, join the book club she is in, even if you don't like to read that much. This shows that you’re willing to work for her approval, and that you not only care about what you are interested in, but what she likes as well. ^{[4]
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- Trying something new to spend time with the woman you like can help you get closer together and maybe even expand your horizons, but don’t confuse taking an interest in her hobbies with changing who you are or doing things you don’t like.
- If the age gap is significant, you may not have that much in common. Exploring her interests will give you a chance to tell if you’d really make a good match, or if you’re just too different.
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Read her body language to determine if she’s interested. Avoid relying solely on her words: for instance, she may be saying nice things, but if her eyes wander off, you can tell she’s losing interest. If she just doesn't seem that into you, don’t try to force it. If she doesn't want to give you her number, or if she never texts you back, move on. There are other fish in the sea.
- If her arms are crossed or her eyes are looking away while you are talking to her, she may not be that into you.
- Make sure your own body language indicates your interest: keep your body squared up with her when you talk to show that your focus isn't elsewhere.
Getting involved in her social circle will help you get to know her better, and it’ll help her get to know you better. If her friends like you, she may start to like you too. Don’t try too hard to win them over if it doesn’t seem like a natural fit, but do make an effort to let her know that the people important to her are also important to you.
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Ask her out in person. Be direct and confident when you ask her out. Make sure to get her phone number, but ask her out in person, not by text or call. Talking in person shows you’re not intimidated by her presence and that you take dating her seriously. ^{[5]
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- Keep it simple and direct: "Hey Linda, I was thinking about going to dinner Friday night and wanted to know if you would like to come with?"

Section 2 of 6:

Dating An Older Woman

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1
Plan your first date somewhere you can get to know each other. Having a nice meal together is a classic first date, and for good reason: everyone loves food, and it gives you a chance to talk and get to know each other. Look at her eyes as you’re speaking and listening. Compliment her on that nice outfit she’s wearing.
- Unless you know your date is particularly shy or awkward, as a general rule, don’t go out to the movies on your first date, because it won’t really give you a chance to talk or even look at each other. When it comes to later dates, movies can be fun experiences and give you two something to talk about.
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Take your time getting physical. The cougar stereotype suggests that all older women want is sex. This is sometimes true—and sometimes not. Go into a first date without any assumptions. The first date might be too early for sex, but it’s a good time to initiate some light physical contact: you can hold her hand, perhaps during dinner, or on the car ride back home. If she’s receptive to small touches like hand-holding, she may be receptive to a kiss goodnight .
- Go in for a kiss slowly, being alert to her body language: if she pulls away or dodges your kiss, she’s not comfortable.
- Limit your first kiss goodnight to about 6 seconds. A longer kiss may make the situation awkward, or make her feel as if you want more. ^{[6]
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- An older woman may make the first move herself, but don’t expect her to.
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Try to avoid feeling jealous of her past relationships. If you’re dating a woman who’s significantly older than you, it’s likely she’ll have dated more and maybe even had more serious relationships than you. She may be divorced or even have children with someone else, but there’s no reason to feel jealous of past partners or to feel insecure about being less sexually experienced. Dr. Behr encourages that you work through all your feelings before committing to an older woman: “There are particular hurdles that [age gap] couples have to go through. So, consider all your feelings about it. Ask yourself, 'How does [this older person] fit into my life as it is currently?'” ^{[7]
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Expert Source

Jessica January Behr, PsyD
Relationship Psychologist

Expert Interview}
- As you continue to date, stay in tune with your needs and desires, and don’t feel pressured to get intimate before you’re ready to. Just go with the flow.
- If you do get intimate, remember to practice safe sex.
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Take the age difference in stride. While the differential will always be there, it’s best not to sweat it. In the end, age differences don’t mean very much. Just relax, get to know her, and pursue the relationship like you would any other. Don’t listen to other people who don't understand the relationship you have. Depending on how much older than you she is, she may be more financially or professionally successful—that’s OK! Don’t feel threatened or insecure about it. ^{[8]
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- Dr. Behr adds, “A lot of the time, older people will be more financially stable. Is that something that affects the relationship? Older people might have children. How do we feel about those dynamics?” ^{[9]
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- Dr. Behr explains how important it is to “be honest with yourself about all the aspects of the relationship.” ^{[10]
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  Jessica January Behr, PsyD
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EXPERT TIP

John Keegan
Dating Coach
John Keegan is a Dating Coach and motivational speaker based in New York City. With over 10 years of professional experience, he runs The Awakened Lifestyle, where he uses his expertise in dating, attraction, and social dynamics to help people find love. He teaches and holds dating workshops internationally, from Los Angeles to London and from Rio de Janeiro to Prague. His work has been featured in the New York Times, Humans of New York, and Men's Health.

John Keegan
Dating Coach

Focus on the perks of dating an older woman—and there are a lot! To start, her confidence and emotional depth create an attractive combination. She can also introduce you to lots of new perspectives based on her life experiences.
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Be fun and spontaneous. Let’s face it: as people get older, they tend to be less spontaneous and exciting. Depending on how old your date is and what other relationships she may have had with people her age, she may be looking for someone who can show her a fun time now and again. Being spontaneous could be as simple as unexpectedly going for ice cream after a date or signing you both up for a muay thai class—basically, anything surprising, unique, and fun. ^{[11]
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- While you may want to keep your first date relatively free of distractions so you can focus on bonding, that doesn’t mean you can’t enjoy a spontaneous dessert or an after-dinner walk in the park.
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Show her you appreciate her throughout your relationship. Whether you’re on date number 1 or your 10th anniversary, continue to shower her with compliments and take her on fun dates to make her feel loved . It’s easy to let the magic of a new relationship fade after a few weeks or months, but treating your special lady right means ensuring the honeymoon phase lasts forever.
- This rule holds true for dating young women as well, but an older woman is unlikely to give you as many chances as a young woman, who may be less self-assured. ^{[12]
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Section 3 of 6:

Where can I meet older women?

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Dating apps Recent research shows that 3 in 10 adults have used a dating app before, and while this number is slightly skewed toward younger people, older people are still logging on and having fun. 37% of singles aged 30 to 49 have used a dating app, while 20% of singles aged 50 to 64 have reportedly looked for love on the World Wide Web. Apps like Match , eHarmony , and Tinder are all great ways to tailor your dating experience to your preferred age range— whether that be 5, 10, or 20 years older than you. ^{[13]
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Pew Research Center
Nonpartisan thinktank conducting research and providing information on public opinion, demographic trends, and social trends
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- Sites like SilverSingles and CougarLife , and apps like Age Gap are specifically designed to meet older people— the internet is your oyster!
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Go to bars with an older crowd It sounds like flirting with 20-somethings at college bars is not at all your vibe, so try to frequent spots with more mature demographics instead. With the exception of the truly eclectic bars that cater to every walk of life, most establishments have specific dynamics and a typical kind of customer. Try to find local bars and restaurants that serve the 35+ crowd, plop yourself on a stool, and spark up a conversation with those around you. Who knows— one of them could be your next conquest! ^{[14]
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Ask friends and family to set you up Prior to the internet, people would be either organically out in public or through friends of friends. Bring this retro move back by asking your friends, family, or other members of your community to introduce you to potential older hotties. Even if they’re not a love match, it’ll give you experience and exposure with an older crowd, which is still a step in the right direction!
- You can similarly look for viable ladies on the Facebook “Friends of Friends” feature.
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Sign up for adult classes Taking an adult class, whether it be cooking, pottery, or salsa dancing, is a great way to meet older singles in your area. Figure out what area or skill you’re most interested in developing and go from there. Sites like Eventbrite offer up monthly schedules of local events, some of which are free! Try your luck at horse-riding, pasta-making, or oil painting with an older cutie by your side. ^{[15]
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Section 4 of 6:

Pros and Cons of Dating An Older Woman

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Pros include emotional maturity, good communication, and life experience. Dating an older woman with a significant age gap can come with a wonderful set of benefits. She’ll likely be very emotionally mature, considering she’s got several years of life experience on you. Additionally, chances are that she’d be a great communicator as her past relationships have hopefully taught her to express herself openly and honestly.
- An older woman will usually have tons of confidence as well, since she’s had a longer time on earth to work on loving themselves. This is good news for you, since she might be willing and ready to share that love with a younger, eager lover. ^{[16]
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Cons include differing life stages, priorities, and judgment from others. When it comes to dating a significantly older woman, you may hit some snags. Depending on the age gap, she may be in a totally different stage of life than you, which can understandably cause some friction.
- Maybe she’s trying to slow down and lead a more peaceful life, while yours is just starting to ramp up. Or maybe she may want to travel more often, which could require a level of financial stability you have yet to achieve.
- Moreover, other people may look at you two together and pass judgment on your relationship, which can be hard to navigate. But honestly— what do they know anyway? Love, after all, is love. ^{[17]
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Section 5 of 6:

Enhancing Your Appearance

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Maintain good hygiene. While this probably goes without saying— take daily showers. Scrub your body with soap and warm water. Wash your hair regularly with shampoo, and apply conditioner so that your hair is nice and soft to the touch. Every woman prefers a partner who can take care of themselves and maintain basic hygiene, but older women won’t tolerate anything less. ^{[18]
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- After you get out of the shower, put some deodorant on.
- You can even add some lotion to your hands to make them extra soft.
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Keep your hair neat and trimmed. Long hair, short hair, bearded, clean-shaven—there’s no right or wrong look, but it’s important to keep your hair and facial hair (if you've got it) neat and clean. Essentially, put effort into your appearance. This won't only attract women; taking a few minutes every day to be intentional about your looks will boost your self-esteem (which is an attractive quality). ^{[19]
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Journal archive from the U.S. National Institutes of Health
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- Trim your body hair only if you want to. The important thing isn't maintaining a specific style, but being neat and clean. This will show older women that you care about your appearance and how you present yourself.
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Brush your teeth twice a day. Older women like to know that their partner takes care of themselves, and that they want their breath to smell nice and fresh. Brush your teeth (for 2 minutes) twice a day, once in the morning and at night. Floss after you’re done brushing in order to get rid of food stuck between your teeth. Then finish off with a mouthwash that cleans your entire mouth and leaves it smelling fresh. ^{[20]
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- Keep breath mints or chewing gum on hand to make your breath minty fresh.
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Apply cologne or perfume in moderation, if desired. If you like to use fragrance, only apply a tiny amount of cologne or perfume to your body’s "pulse points." These are spots where blood vessels are close to the skin, including under your arms, behind your knees, around your neckline, and on your wrists. When you apply scent to your pulse points, the blood creates heat, which allows the fragrance to smell stronger. However, it’s very important that you don’t put too much on. A lot of cologne or perfume can turn anyone away. ^{[21]
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- There’s nothing wrong with not wearing any scent—in fact, some women prefer a partner who doesn’t wear any fragrance. Just shower regularly, and you’ll smell great. You could even opt for scented soap over cologne or perfume.
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Select a stylish and fresh wardrobe. There’s no right or wrong way to dress, but as a general rule, if you’re after a specific woman, try to match her style: many older women are attracted to someone who dresses similarly to themselves. If she wears belted shorts with a polo, she might be into the more "preppy" look. If she wears jeans and T-shirts all the time, she might prefer a partner who sports a more relaxed look. ^{[22]
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- Make sure all of your clothes are ironed. This shows women that you care about the way you appear to the outside world and that you care about yourself. Try to avoid looking as if you just rolled out of bed.
- Variations on appropriate attire are natural when it comes to individuals. There is no "perfect" wardrobe. Use your judgment, and try your best. It never hurts to go out and buy some new shirts or pants if you don't have much in your closet.

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How can I tell if an older girl likes me or not?

Cher Gopman
Dating Coach
Cher Gopman is the Founder of NYC Wingwoman LLC, a date coaching service based in New York City. 'NYC Wingwoman' offers matchmaking, wingwoman services, 1-on-1 Coaching, and intensive weekend bootcamps. Cher is a Certified Life Coach, a former psychiatric nurse, and her work has been featured on Inside Edition, Fox, ABC, VH1, and The New York Post.

Cher Gopman

Dating Coach

Expert Answer

Pay attention to her body language while you're talking to her to see if she's interested. If she maintains eye contact, plays with her hair, or smiles a lot, she may like you.

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She might be concerned about what her friends may think of her dating a younger person. Hopefully, this shouldn’t stop you two from dating. Be patient if she's hesitant, and remember that it's ultimately nobody else's business.

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How to Woo an Older Woman: 18 Tips for Winning Her Over

How to Attract an Older Woman

Steps

Getting to Know Her

Dating An Older Woman

Where can I meet older women?

Pros and Cons of Dating An Older Woman

Enhancing Your Appearance

Video

Expert Q&A

Tips

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