Getting Her Attention
Carry yourself with confidence. When you approach an older woman, hold your head high, roll your shoulders back, and straighten your back. This will help you have an air of confidence that will make you seem appealing to someone who's a little more mature. Try giving yourself a pep talk before you walk up to her. For example, you might tell yourself something like, "I'm cute, smart, and funny, so I just need to be myself!" Older women tend to prefer partners who are confident—in addition to being more confident themselves, they've had plenty of time to experience the hangups that come along with insecurity. Also, if you come across as insecure, it could make you seem like you're looking for a mother figure, rather than a partner.
Make eye contact when you talk to her. One of the best ways to show confidence is by maintaining eye contact. However, don't just stare at her straight in the eyes, as that can seem creepy. Hold her gaze for a few seconds, then look away for a moment. To seem even more flirtatious, look her in the eyes, give her a smile, then glance at her lips for a moment.
Give her a sincere compliment. As you're talking to your new interest, pay attention to exactly what it is that's drawing you to her. Then, turn that into a sweet compliment that's unique to her. If possible, try to focus on how she makes you feel or the qualities she projects. Those types of compliments can be a lot more meaningful than just a comment on her physical appearance. For example, if you love the warm way she laughs, you might say something like, "I feel like I'd never stop smiling around you, you're so much fun!" If you do want to compliment her appearance, try choosing something that's a stylistic choice, like her hair or her clothing. Mentioning that you love her smile or her eyes can be sweet, but those compliments can be a little generic—it might work in your favor to be a little more creative. For instance, if she's telling an interesting story, you might say, "I could listen to you talk all day!"
Avoid mentioning her age at first. In general, it's best to avoid bringing up a woman's age altogether, but that's especially true when you're flirting with an older woman. Talking about how she looks great for her age might make her feel self-conscious, or it might emphasize the fact that you're younger than she is. Eventually, the subject of your age difference will likely come up, and you don't have to shy away from the conversation. Just don't make it your main focus early on. If she does mention her age, you can say something like, "I never would have guessed." If she asks you how old you think she is, always guess a few years younger than you actually think. Don't be too obvious about it, though. If you think she's in her mid-30s, for instance, a good guess might be 29. Once you do start talking about her age, you can ask how a woman her age got to be single, or how she's kept so many partners at bay. Just don't make it sound too corny or put on.
Make yourself seem independent. Older women appreciate partners who are able to take care of themselves, so emphasize your accomplishments and the things you like to do on your own. If you're always talking about your friends and family, then she may not see you as someone who stands on their own two feet, which can be a big turn off for women of any age. For instance, you might talk about the things you love to do for fun, your favorite sports, your favorite hobbies, or just the things you do or have done on your own to develop your character. If you have a good career with a bright future, talk about what you do for a living. However, don't brag—being arrogant can actually make you seem less confident. If you live with your parents, try to avoid mentioning that, especially if she's closer to their age than she is to yours.
Be direct and ask her out. If the conversation is going well and you're interested in getting to know this lady more, don't play games—let her know. Older women tend to appreciate a more direct approach. Stay cool, and casually ask her if she'd be interested in seeing you again the following week. Try saying something like, "I've loved talking to you, but I have to get going. Are you free for dinner next Friday?" If she says yes, ask for her phone number. If she says no, don't panic—just ask her if there's another night she'd like to meet. Remember to smile and look her in the eyes when you ask her out!
Taking Her Out
Plan a nice date based on what you learn about her. Before your date, spend a little time texting or talking so you can get a feel for what she likes. Then, arrange a nice date based on that. Just remember to plan around what you're comfortable with, too—if you're too far out of your comfort zone, it will be obvious. For instance, if she likes fine dining and you're comfortable with it, you might take her to an upscale restaurant in your area. However, if you can't afford the bill or you aren't comfortable in a fine dining setting, the date may feel awkward, so it would likely be best to plan something else. Try to think of dates that she might not be expecting. For instance, if you're outdoorsy, you might plan a casual hike or an evening boat ride.
Put effort into looking your best to impress her. Before your date, make sure you have a chance to shower and put on a nice outfit. Showing up in wrinkled clothing or having messy hair might send the impression that you don't take the date—or her time—very seriously. Try wearing a light spritz of perfume or cologne to ensure you smell good through the whole date. Just don't overdo it—strong smells can be offputting, even if they're pleasant.
Hold the door for her. Some women aren't crazy about chivalrous gestures—they don't want to be made to feel helpless. However, for other women, it's a sign of respect and they'll be expecting it. To be sure you don't make the wrong move, make an offer to open her car door, hold the door at the restaurant, or order a drink for her at the bar. Then, gauge her reaction to see if she likes that type of treatment. If she does seem to appreciate the gesture, look for little ways to continue being chivalrous, like offering to carry something heavy for her. If she declines your offer, just smile and appreciate the fact that she's secure in her independence. Remember that in any case, there are times when it's polite to open or hold a door for someone, regardless of whether you're dating them or not.
Avoid talking about things that emphasize a generation gap. Even if she's savvy, an older woman might not know all of the newest street slang or latest memes, and she's not likely to be impressed by stories about the killer keg stand you did a few nights ago. Instead, try to talk about your interests that are more likely to align with hers, like politics, world events, books, films, and music. For instance, if you've traveled, try talking about some of the places you've been and the things you enjoyed about them. If you haven't traveled much, try talking about the places you'd like to go.
Embrace your younger age. If you're trying to impress an older woman, you might feel embarrassed or shy about the fact that you're younger. However, try to remember that you have a lot of advantages that someone her own age might not have, like more physical energy and an enthusiasm for trying new things. Keep in mind that if she's accepted a date with you, she's likely intrigued by your youth, and she's obviously interested in getting to know you for who you are. You might benefit from acting more mature around her, but don't feel like you have to pretend to be someone you're not! Call attention to your strengths instead of pointing out your weaknesses. Don't talk about your lack of experience or job prospects. Instead, talk about how excited you are for the future and about how happy and free you are at your age.
Flirt with her throughout the date. One of the best ways to build sexual tension is to break the touch barrier, so look for little opportunities to brush your hand or leg against hers while you're out together. In addition, give her compliments, make eye contact, and smile at her while she's talking. If you can feel the chemistry building, continue to escalate the flirting. For instance, if you touch her arm and she puts her hand on your knee, you might move your chair a little closer to hers and rest your leg against hers. If she seems like she's pulling back a little, you may be coming on a little strong, or the chemistry might just not be right. Try switching back to a more friendly demeanor, rather than a flirty one. Then, ease back into flirting once she seems more comfortable.
Becoming Intimate
Kiss her at the end of the date if things are going well. Older women tend to appreciate a direct approach, so if you're enjoying yourself and you want to take her to bed, you may not need to take the slow approach. As the end of the evening approaches, if you're feeling a spark between the two of you, go in for a kiss. If she kisses you back, let the kiss become passionate for a few moments, then break it off and pull back a little. If you're not sure if it's okay to kiss her, try leaning your face close to hers while you glance at her lips. If she leans in as well, it's probably okay to kiss her. If you're still not sure, though, try softly saying, "I'd love to kiss you right now." By pulling back at the peak of the kiss, you'll give her a chance to think for a moment, but it will also leave her wanting more.
Ask her if she'd like to continue the date. If you kiss her and things are still going well, be bold and make a move to take things to the bedroom. For instance, if you're dropping her off at home, you might say something like, "I'm having such a great time, and I really don't want this night to end. Could I come inside with you?" Some women prefer not to become intimate with a partner until they've been on a few dates together. If you think that may be the case, wait until you're sure she's comfortable before you try to sleep with her. Remember not to ever be pushy when you're trying to go to bed with a woman. If she says no, or even if she hesitates, smile confidently and say something like, "That's okay, I'll really be looking forward to seeing you again. Give me a call tomorrow, okay?" Try suggesting a hotel room if she seems uncomfortable going to your home or inviting you to hers.
Join her inside if she seems open to intimacy. If she invites you into her home, or if she agrees to join you at your home or a hotel room, meet her indoors, then kiss her again firmly. Show her that you know exactly what you want, but also be open to whatever signals she's giving you. For instance, some older women really enjoy instructing a younger partner, while others might prefer you take the lead with your youthful enthusiasm.
Move confidently in the bedroom. Even if you don't have much experience in bed yet, try not to come across as insecure or shy. Instead, kiss her firmly, and enjoy exploring each other's bodies in a fun and intimate way. Don't rush—remember, especially for someone who's more mature, sex is more about the journey than the destination. If there's anything that doesn't go well, like if you find yourself fumbling with her bra strap, just laugh about it and keep going. Don't get in your head about your lack of experience. Pay close attention to any signals she gives you. For instance, she may direct you to do something she likes, or she may tell you that she doesn't like something. On the other hand, she may not say very much. In that case, pay attention to whether she leans in to whatever you're doing, which probably means she likes it, or whether she pulls away slightly.
Make her want you again. After you've taken her to bed, you should leave on a good note. Tell her how much you enjoyed yourself, and let her know you'd like to see her again. Then, follow up with a text or a call a day or two later. If you're interested in a relationship, call her the next day. If you'd prefer to keep things casual, wait a couple of days, instead. Either way, be upfront about your intentions. If she's interested in the same thing as you, she'll let you know.
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