Dating women, regardless of their age, is always a joyful experience, but it becomes even more special with mature women. They tend to be more self-assured because they know exactly what they want, which makes them incredibly alluring. Whether you're curious about dating older women or have a crush on someone special, staying confident and composed is key to capturing her attention.
Steps
Grab Her Attention

Be confident. When approaching an older woman, stand tall, chest out, and back straight. This posture makes you appear confident and attractive to someone who is more experienced.
- Reassure yourself before making a move. For instance, tell yourself, “I am charming, intelligent, and fun, so I’ll just be myself!”
- Older women often prefer confident partners, as they themselves are confident due to having overcome insecurities. If you seem insecure, it might come across as seeking a mother figure rather than a romantic partner.

Maintain eye contact during conversation. One of the best ways to show confidence is by looking into the other person's eyes.
- However, avoid staring intensely, as it can come off as too obvious. Glance at her eyes for a few seconds, then look away naturally.
- To add a flirtatious touch, smile while holding her gaze and briefly glance at her lips.

Offer genuine compliments. When talking to someone you’re interested in, pay attention to what draws you to her and give her a sweet, thoughtful compliment. Focus on her personality or the way she makes you feel, as these carry more weight than comments about her appearance.
- For example, if you love her warm laugh, you could say, “I can’t help but smile whenever I’m around you—you’re such a joyful person!”
- If you want to compliment her looks, focus on her style, like her hairstyle or outfit.
- While saying you love her smile or eyes is sweet, it’s a bit common—try to be more creative. For instance, if she tells an engaging story, you might say, “I could listen to you talk all day!”

Avoid bringing up her age early on. Generally, it’s best to steer clear of mentioning a woman’s age, especially when pursuing an older woman. Saying she looks younger than her age might make her uncomfortable or highlight the age gap. Over time, the topic will naturally come up, but there’s no need to address it right away.
- If she mentions her age, you could respond with, “I honestly wouldn’t have guessed.”
- If she asks you to guess, always guess a few years younger than you think. In this case, honesty isn’t the best policy—if she looks 35-36, guess around 29.
- When discussing her age, you might ask why she’s still single or why she’s not swayed by her admirers, as long as you avoid sounding childish or overly dramatic.

Be independent. Older women appreciate partners who can take care of themselves, so highlight your achievements and the things you enjoy doing on your own. If you constantly talk about relying on friends or family, she might see you as dependent, which can be a turn-off.
- For example, share hobbies, sports, or activities you enjoy, or talk about how you’ve worked on personal growth.
- If you have a stable career with a bright future, mention your work—but avoid bragging, as arrogance can come off as insecurity.
- If you live with your parents, avoid bringing it up, especially if she’s close to their age.

Be direct about asking her out. If the conversation is going well and you’d like to get to know her better, don’t beat around the bush—let her know. Older women often appreciate straightforwardness. Stay calm and suggest meeting up the following week.
- You could say, “I’ve really enjoyed talking to you, but I have to head out now. Would you like to have dinner with me next Friday?” If she agrees, ask for her number. If she declines, don’t worry—you can always suggest another time.
- Remember to smile and maintain eye contact when you ask!
Dating

Plan the date based on what you’ve learned about her. Before the date, take some time to text or chat with her to get a sense of her interests. Organize the date around what you discover, but ensure it stays within your comfort zone—she’ll notice if you’re uneasy.
- For example, if she enjoys fine dining and you’re comfortable with it, take her to an upscale restaurant. However, if it’s beyond your budget or makes you uncomfortable, the date will feel forced; opt for a different plan instead.
- Try to plan a date that surprises her. For instance, if you love outdoor activities, suggest a picnic or an evening walk.

Groom yourself to make a good impression. Before the date, shower and dress neatly. Showing up in wrinkled clothes or messy hair might make her think you don’t care about the date or her time.
- Apply a bit of cologne or deodorant to stay fresh throughout the date, but avoid overdoing it, as strong scents can be off-putting.

Hold the door for her. Some women don’t mind chivalrous gestures—they don’t want to feel helpless. Others, however, see it as a sign of respect and expect it. To avoid missteps, offer to help her with her coat, open doors, or order drinks at the bar, then observe her reaction to see if she appreciates it.
- If she seems to like your gestures, continue being chivalrous, such as offering to carry heavy bags.
- If she declines, smile and respect her independence.
- Remember, holding doors for others is often just polite, regardless of whether you’re dating them.

Avoid topics that highlight the generation gap. Even if she’s well-informed, she might not know the latest slang or viral memes, and she may not be impressed by stories of your recent handstand attempts. Instead, focus on interests that align with hers, such as politics, global events, books, movies, or music.
- For example, talk about places you’ve traveled to and what you enjoyed there. If you haven’t traveled much, share destinations you’d like to visit.

Embrace being younger. When trying to impress an older woman, you might feel self-conscious about your age. However, remember that you bring unique advantages, like physical energy and enthusiasm for new experiences, that someone her age might not have.
- If she agrees to date you, it means she’s intrigued by your youth and genuinely wants to get to know you better. You might earn extra points by acting mature around her, but don’t feel like you have to pretend to be someone else!
- Focus on your strengths rather than highlighting your weaknesses. Avoid talking about lack of experience or career prospects. Instead, share your optimism for the future and the joy and freedom you currently enjoy.

Flirt with her throughout the date. One way to build intimacy is by breaking the touch barrier, so look for opportunities to casually touch her hand or leg during the date. Additionally, compliment her, maintain eye contact, and smile while talking.
- If you sense mutual attraction, keep flirting. For example, if you touch her arm or she places her hand on your knee, move closer and let your legs touch.
- If she keeps her distance, you might be coming on too strong, or the connection isn’t there yet. Shift to a friendlier approach and resume flirting when she seems more comfortable.
Getting Intimate

Kiss her at the end of the date if things go well. Older women often appreciate directness, so if you’re feeling the chemistry and want to take things further, don’t hesitate. After some light flirting, if you feel drawn to each other, go for the kiss. If she reciprocates, keep the kiss passionate but brief, then pull back slightly.
- If you’re unsure, lean in close and glance at her lips. If she leans in too, it’s a sign she’s open to a kiss. If you’re still unsure, whisper, “I really want to kiss you.”
- Ending the kiss at its peak leaves her wanting more and builds anticipation.

Ask if she wants to continue the date. If the kiss goes well, take the initiative to suggest extending the date in a more private setting. For example, when dropping her off, you could say, “I’ve had an amazing time, and I don’t want the night to end. Can I come inside?”
- Not all women are comfortable getting intimate early on. If you think she’s one of them, wait until you’re sure she’s ready before making a move.
- Never pressure her. If she declines or hesitates, smile confidently and say, “No worries, I’m already looking forward to seeing you again. Call me tomorrow?”
- Suggest a hotel if she seems uncomfortable with going to your place or inviting you to hers.

Stay with her if she wants to get intimate. If she invites you inside, agrees to go to your place, or suggests a hotel, join her and kiss her passionately again. Let her know what you want, but also be open to the signals she’s sending.
- For example, some older women enjoy guiding younger partners, while others appreciate the energetic enthusiasm you bring.

Move to the bedroom confidently. Even if you lack experience, don’t show insecurity or awkwardness. Instead, kiss her deeply and enjoy exploring each other’s bodies with playfulness and intimacy. Take your time—mature individuals value the experience over rushing to the finish line.
- If something goes wrong, like fumbling with her bra, laugh it off and keep going. Don’t dwell on inexperience.
- Pay attention to her cues. She might guide you to what she likes or tell you what she doesn’t. If she stays silent, observe whether she leans into your actions, a sign she’s enjoying it, or pulls away.

Leave her wanting more. After your time together, send her a thoughtful message. Let her know how much you enjoyed it and that you’d like to see her again. Follow up with a text or call within a day or two.
- If you want a serious relationship, call her the next day. If you’re not ready for commitment, wait a couple of days. Either way, be clear about your intentions. If she feels the same, she’ll let you know.