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How to attract older women: Tips for younger guys to flirt with single women and divorcees

Updated on July 30, 2013
Crushing over a woman who is in her thirties or forties?
Crushing over a woman who is in her thirties or forties? | Source

How to attract older women? To flirt with a woman in her 30s or 40s, stop thinking about your sex appeal and start thinking about how you can be a mature, charming and good looking young guy. Popular culture portrays older women as cougars who run after hot younger men. This post avoids such trashy misrepresentation of dating and being in a relationship with older women. It focuses on real advice for young men who want to impress older single women and divorcees who are in their thirties and forties.


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 meeting you often. The easiest way to move past this hurdle is to find common interests and stuff that you can do together.


If you don't have common interests, you may have to develop a new hobby just so that you can get closer to her. Don't do this with a malicious intent. The purpose of doing this is just so that you both can interact without making your meetings awkward. Here are a few nice ways in which you can spend time with an older woman without giving your first few meetings the seemingly heavy tag of 'dating'.

  • Exercise together at the gym – bonding and flirting with her at the gym is a good way to ease out all the awkwardness
  • Go to yoga classes together
  • Watch plays at the theatre
  • If she has a reading hobby, meet her at the book store at the pretext of shopping for books
  • Take up hobby classes and workshops together


2) Dress like a man: Look handsome and decent

A woman in her thirties or forties will not expect a younger guy to dress like a man in his thirties or forties. But she doesn't expect him to dress like a rebellious teenager either. Here are tips for guys in their twenties.

  • Regardless of the type of underwear you have on, don't wear your pants below your underwear
  • Prefer 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


Compliment a woman to make her feel like sexy and young all over again.
Compliment a woman to make her feel like sexy and young all over again.

3) Compliment her heavily: Make older women feel attractive

Older women in their 30s and 40s constantly battle body image issues. Just like men, age takes a toll on their bodies and they are looking for ways to keep fit and look sexy.


You can attract an older woman simply by giving her endless and genuine compliments. Don't be shy about being direct and tell her what you like about her attractiveness. Use the word Girl instead of Woman when you compliment her. 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 and act like well mannered guy

The typical image of a cougar portrayed in TV series 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 trashy behavior is generally not that common.


Don't be 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 at the same time.


5) Don't be the loudest guy in the room: Be calm

Being an alpha male and shouting your lungs out may make you seem macho in front of your other friends. It may even make you the center of attraction in a party and help you flirt with girls of your age. But this tactic may not work when you want to impress an older woman.


Older women like young guys who are calm. They are unlikely to feel attracted towards the loudest brat because that is a sign of immaturity.


6) Listen: Let an older woman take charge of a conversation

Women love it when men take the initiative to start conversations whether it is 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.


Women in their thirties or forties may have gone through bitter divorces and toxic relationships. After all the mess, they may be looking for a man who can be a good listener. Show her that you can be the boy who makes her have fun and patiently listens to her at the same time.


Make her happy by showing her the youthful side of life. Make her re-live her bygone years.
Make her happy by showing her the youthful side of life. Make her re-live her bygone years.

7) Be fun and spontaneous: Remind her of her youthful days

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 that she has not done since a long time.


For example, even something as simple as randomly going out for ice cream at midnight will give her a rush which she hasn't experienced in a long time. Any activity which includes spontaneity will get an older woman's heart racing, no matter how silly it seems.


8) Be a gentleman: Show an older woman your chivalry

Older women who have been through marriages and long relationships may have become strangers to chivalry. Their husbands may not have been flirting with them, 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 that you can do.

  • Open doors for her
  • Compliment her continuously
  • Pull out chairs for her
  • Stand up when she enters


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 were probably missing from her life.


9) Don't point out the age difference while talking to an older woman

The worst thing you can do while flirting with an older woman is to point out the age difference. Even if it is not intentional, mentioning the age difference can instantly put her off.


Think from her perspective - just the mention of the words 'age difference' can trigger many nasty questions and thoughts in her head. Below are some of the things that she could be thinking 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 with such a big age difference?
  • Will I be labeled as a cougar if everyone finds out that I am dating this young 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 panic thoughts in her head and don't mention your age difference. Choose your words carefully every time you talk about age.


10) Be mature for your age

If an older woman has the slightest of crush on you, she will instantly be attracted to you if she feels that you are way more mature than how old you actually are.


For example, you will impress a woman in her 30s or 40s if you are just twenty five, and yet you have a good job, car and the vision to be successful in life. Your maturity will show her that you are not an immature kid who has no sense of life at all.


11) Stop imagining an older woman as someone who just wants sex

Cougars are portrayed in popular culture as women who just want sex. You must remind yourself that to attract an older woman, you will have to move past this notion and try to establish a relationship of substance.


Unless you acknowledge that your relationship with an older woman will be a lot more than just lust, you will never be able to present yourself as a man of substance.


12) Don't brag about having more partners than her: An older woman will see right through

An older woman won't be turned off if you honestly admit that you have had fewer partners than her. Since she is many years older to you, she expects herself to be more experienced. Remind this to yourself 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 has had way more experience and she will instantly be able to spot all the lies.


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