How to Date an Older Woman

1. Be a gentleman. If you want to successfully date an older woman, then you have to be a true gentleman.

   You don’t want her to think that you don’t have manners or that you don’t know how to treat a woman.

   Now, some women think that certain “gentlemanly” traits, such as holding doors or pushing out chairs, are antiquated, so try to get a read on her expectations.

   Still, it doesn’t hurt to be polite, to have good manners, and to avoid overly vulgar topics.

   If you want to be a true gentleman, the most important thing is that you’re respectful of your date.
   • Show up to your dates on time and sometimes even with a small gift.
   • Make sure to put an effort into your appearance before you go on a date. You want the older woman to see that she’s worth it.
   • Give her compliments to show how beautiful and amazing you think she is.
   • Treat everyone around you with respect as well. Being kind and polite to servers, friends, and strangers shows that you’re a respectful person and that you’re not just putting on an act for the woman.
    
2. Don’t worry about your lack of experience. Sure, the older woman has probably had more life experience and has been with more people than you have.
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   That doesn’t mean you have to talk about it all the time or worry that you don’t have enough to bring to the table.

   If she’s more experienced in the bedroom, then great—enjoy whatever it is that she’s going to teach you.

   Try not to focus on your past and think about enjoying the experience you’re gaining with the older woman in the present.
   • If you want to be a good boyfriend, then you really don’t have to bring up your lack of experience. For one thing, it may make the older woman feel self-conscious about the amount of experience she has. For another, it’ll make you look insecure.
   • When you’re getting intimate, try not to worry about it if you don’t have very much experience in that department. If you obsess over this, then it’ll keep you from enjoying yourself.
    
3. Be assertive. Be a man who knows what he wants and isn’t afraid to ask for it.

   If you’re always second-guessing yourself, mumbling, or waiting to say what’s really on your mind, then your older woman may start looking for someone more assertive.

   Get comfortable telling her what you’d like to do on your dates, letting her know if she hurt your feelings, and asking for what you want.
   • Part of being assertive means having a firm, clear voice when the time comes to say something. If you talk too quietly or stumble over your words a lot, then you’ll have trouble being assertive.
   • While you shouldn’t interrupt the older woman when she’s talking, you should be comfortable with articulating what’s on your mind when it’s your time to talk.
    
4. Be mature. Though you may not be the most mature guy in the world, you can certainly make an effort to become more worldly.

   Avoid having temper tantrums, getting angry over stupid little things, or just generally looking like you have no idea what’s going on.

   Make an effort not to look clueless and to read up on something if you don’t have any idea how it works.

   Learn to be polite to others and to treat them with respect instead of just looking out for yourself. Your older woman will want a man who is mature enough for her.
   • Avoid whining or complaining about insignificant matters too much. This is a sign of a true lack of maturity.
   • Avoid childish habits such as biting your nails, making fun of people, or fighting with your siblings.
   • Try not to get overly angry or upset when things don’t go your way.
    
5. Keep things fun and light. The older woman you’re dating may have had her fair share of serious older men.

   You can show her that you’re different by keeping things upbeat, fun, and lighthearted, so that she enjoys your time together.

   Minimize the serious talks and conversations about “Where is this going?” if you know what’s good for you.

   Work on enjoying your relationship in the moment instead of worrying about what lies ahead.
   • Stick to fun, lighthearted topics and make her laugh. Show her how much fun you can be.
   • Of course, you can open up to her and share more serious things about yourself when you’re ready. But as a rule, you should keep things fun and easy.
    
6. Don’t bring up your age difference all the time. If you want the relationship to last, then you can’t go around talking about how much older than you she is all the time.

   You want her to see that you want her for her, instead of because you think it’s hot and exciting to date a woman who is older than you.

   If you keep bringing it up, then she’ll get the sense that your heart isn’t in the right place.
   • Fine, if she brings it up and wants to laugh about it, then you should join in. But if she doesn’t mention it, then neither should you.
    

    Making It Last

   

1. Show a real interest in who she is. If you really want to have a successful and long-lasting relationship with an older woman,

   then you have to do more than just think of her as that sexy older woman you’ve been seeing. You have to make an effort to get to know the person who she really is and to remember that age is just a number.
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   Let her see that you care about getting to know her and that you truly value the time you spend together. Here’s how:
   • Take the time to really listen to her when she talks to you. Put away your phone, make eye contact, and don’t interrupt her.
   • Ask her questions about her childhood, her work, her friends, her family, and the things that interest her. Show her that you really want to know everything about her.
   • Check in with her when you’re apart to show that you care about how her day is going and that you’re thinking of her.
   • Give her compliments that show her that she really stands out to you. Don’t just tell her she’s hot; compliment her sense of humor or other aspects of her personality that really matter.
    
2. Give her space. If you want to make your relationship last, then you can’t be clingy.

   You have to respect the fact that your older woman is her own person and that she has a life going on outside of being with you.

   This could mean her time at work, spending nights with her girlfriends, or all of the time she spends doing her own thing, whether it’s yoga, writing poetry, or cooking.

   Don’t be needy or ask her to hang out with you all the time, and appreciate the fact that she has a life outside of your relationship.
   • Show an interest in the things she does when you’re not together. Ask her about her friends, her job, and her hobbies to show that you care.
   • You can check in with her when you’re apart, but don’t call her three times when she’s hanging out with her girlfriends; you don’t want her to think that you have nothing else going on or that you’re jealous.
    

Be on the lookout for new restaurants to try, new places to visit, and new activities to try together, from taking salsa lessons to cooking an Italian meal together.

If you get too comfortable doing the same thing together day after day, then you may come off as complacent and the older woman, who has more experience, may be wanting something more.