- Show the older woman you’re invested in who she is as a person by asking her questions about herself and taking an interest in her hobbies.
- Attract her attention by presenting yourself well: maintain proper hygiene and a good sense of style.
- 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.
Getting to Know Her
Flirt respectfully. 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.
Be confident. 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. 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.
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.
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 give you an opportunity 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. 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.
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.
Make friends with some of her friends. 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.
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. 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?"
Perfecting Your Look
Maintain good hygiene. 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. 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.
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). 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.
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. Keep breath mints or chewing gum on hand to make your breath minty fresh.
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. 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.
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. 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.
Dating Her
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.
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. An older woman may make the first move herself, but don’t expect her to.
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. 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.
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.
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. 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.
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.
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