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.
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.
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!”
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.
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.
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!
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.
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.
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.
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.
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.
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.
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.
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.
For instance, some older women really enjoy instructing a younger partner, while others might prefer you take the lead with your youthful enthusiasm.
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.
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.
