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How to Flirt With Single Older Women and Divorcées
How can you attract middle-aged or older women? To flirt with a woman in her 30s, 40s, or beyond, stop thinking about your sex appeal and start thinking about how you can show that you are a mature, charming, and attractive young guy.
Pop culture portrays older women as cougars who chase after hot younger men. This article avoids these misrepresentations of dating and being in a relationship with an older woman. It instead focuses on real advice for young men who want to impress single older women and divorcées in their 30s, 40s, and beyond.
12 Tips for Attracting Older Women (and Making a Relationship With Her Work!)
- Find common interests or things you can do together.
- Dress respectably.
- Compliment her heavily to make her feel attractive.
- Be polite; act like a well-mannered guy.
- Don't be the loudest guy in the room—be calm.
- Listen—let her take charge of the conversation.
- Be fun and spontaneous—remind her of her youth.
- Be a gentleman—show her you can be chivalrous.
- Don't point out the age difference when talking to an older woman.
- Act mature for your age.
- Stop thinking she just wants sex.
- Don't brag about your sexual experience—she'll see right through you.
1. Find common interests or things you can do together.
Even if an older woman is attracted to you, the age difference may be holding her back from getting together with you often. The easiest way to move past this hurdle is to find common interests and things that you can do together.
Here are a few nice ways you can spend time with an older woman without giving your first few meetings the seemingly heavy label of "dating":
- Exercise together at the gym—bonding and flirting with her at the gym makes for a fun, casual outing.
- Go to yoga classes together.
- Attend plays at the theatre.
- If she enjoys reading, meet her at a bookstore to browse.
- Take up hobby classes or workshops together.
2. Dress respectably.
A woman in her 30s or 40s does not expect a younger guy to dress like a man in his 30s or 40s, but she doesn't expect him to dress like a rebellious teenager, either. Here are a few style tips for guys in their 20s:
- Regardless of the type of underwear you have on, don't wear your pants below your underwear.
- Wear button-up or dress shirts instead of casual t-shirts.
- Jeans are a safe fashion bet.
- Avoid wearing extreme drop-crotch trousers.
- If you are a guy who likes to accessorize, don't wear too much bling.
- Don't wear your hair in eccentric hairstyles.
3. Compliment her heavily to make her feel attractive.
Older women constantly battle body-image issues. As with men, age takes a toll on their bodies, and they might be looking for ways to stay fit and look sexy.
You can attract an older woman simply by giving her endless genuine compliments. Don't be shy about being direct and telling her what you like about her and what you find attractive. Some women may enjoy being referred to as "girl" rather than "woman." Here are a few examples.
- "I am the luckiest guy in this room because I am sitting with the hottest girl."
- "Your curves look perfect in that little black dress."
- "Wow, you look sexy in those skinny jeans!"
- "You should be a model for Victoria's Secret."
- "You are the hottest girl I have ever seen."
4. Be polite; act like a well-mannered guy.
The typical image of a cougar portrayed in TV shows and movies is that of a woman who goes to bars to seek out men, flings, and one-night stands. Like most glamorous things that happen only in the movies, this sort of behavior is not necessarily typical.
Don't act like a bad boy in front of an older woman. Be polite and well-mannered around her if you want to attract her. She is looking for a young man who can show her a good time, but she doesn't want to get into trouble.
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5. Don't be the loudest guy in the room—be calm.
Acting like an alpha male and hollering at the top of your lungs may make you seem macho in front of your other friends, and it may even make you the center of attention at a party or help you attract girls your age. But this tactic may not work when you want to impress an older woman.
Older women like younger guys who are calm. They are unlikely to feel attracted to the loudest man in the room because they recognize noisiness as a sign of immaturity.
6. Listen—let her take charge of the conversation.
Women love it when men take the initiative to start conversations, whether it is at a date or a casual first meeting. But once you have broken the ice, judge the older woman's body language, and let her take charge of the conversation.
Older women may have gone through bitter divorces and toxic relationships. After all the drama, they may be looking for a man who is a good listener. Show her that you can be the boy who has fun with her and patiently listens to her at the same time.
7. Be fun and spontaneous—remind her of her youth.
Spontaneity generally dies down as people get older. You can attract an older woman by giving her a chance to re-live her youth. Be spontaneous, and do the silly little things she hasn't done for a long time.
For example, even something as simple as randomly going out for ice cream late at night will give her a rush she hasn't experienced in a long time. Any activity that's done spontaneously will get an older woman's heart racing, no matter how silly it seems.
8. Be a gentleman—show her you can be chivalrous.
Older women who have been through marriages and long-term relationships may have become strangers to chivalry. Their husbands may not have been flirting with them toward the end of the marriage, leading to a dip in levels of romance.
Attract an older woman by flirting with her and behaving like a gentleman. Here are a few things you can do:
- Open doors for her.
- Compliment her continuously.
- Pull out chairs for her.
- Stand up when she enters the room.
Give her the thrill of being the center of attention again, and behave like a complete gentleman around her. These are some of the playful and romantic little things that have probably been missing from her life.
9. Don't point out the age difference while talking to an older woman.
The worst thing you can do when flirting with an older woman is point out the age difference. Even if it is not intentional, mentioning the age difference can instantly put her off.
Think about it from her perspective—just the mention of the words "age difference" can trigger uncomfortable questions and thoughts in her head. Below are some of the things that she could be thinking about when the age difference is pointed out to her.
- "What am I doing with a man half my age?"
- "What will my kids think of me dating a guy who's closer to their age than mine?"
- "Will I be called a 'cougar' if everyone finds out I'm dating this younger guy?"
- "What if my friends make fun of me when they hear about the age difference?"
- "Am I getting into a rebound relationship with this guy who is so young?"
Avoid triggering these panicked thoughts in her head—don't mention the age difference. Choose your words carefully whenever you talk about age.
10. Act mature for your age.
If an older woman has even the slightest crush on you, she will instantly be attracted to you if she feels that you are way more mature than your actual age.
For example, you will impress a woman in her 30s or 40s if you are just 25, yet you have a good job, car, and a plan for career success. Your maturity will show her that you aren't an immature kid with no life experience.
11. Stop thinking she just wants sex.
In pop culture, cougars are portrayed as women who just want sex. You need to remind yourself that to attract an older woman, you'll need to move past this notion if you want to establish a relationship of substance.
Until you acknowledge that your relationship with an older woman will be a lot more than just lust, you'll never be able to present yourself as a man of substance.
12. Don't brag about your sexual experience—she'll see right through you.
An older woman won't be turned off if you honestly admit that you have less sexual experience than she does. Since she is older than you, she expects you to have less experienced. Remind yourself that you don't need to over-inflate your sexual history if you are faced with the question, "So how many women have you been with in the past?"
Don't make the mistake of bragging about your experience in bed to an older woman. Remember that she is more experienced, and she will instantly be able to spot all the lies.
I hope that you have found the advice in this article useful. Remember that being respectful and a good listener is the best way to any woman's heart, no matter how old she is. Every woman is different; not all of these tips will work for every woman or relationship.