Flirting with an Older Woman

Flirting with an older woman can be intimidating.  Often they exude more confidence than younger women and they can be more independent.  This can make them harder to approach.  They tend to have a better idea of who they are and what they want.  These same reasons are exactly why it can be fun to flirt with an older woman.

Make some eye contact with the lady you would like to talk to.  Smile at her for a few seconds, look away, and then repeat once or twice.  If she smiles back, show that you’re open to conversation.  Don’t stand with your arms crossed and move away from your friends for a few minutes if you’re part of a group.  This will give her a chance to approach you if talking to someone in a group is daunting.  If she doesn’t come to say hello, you have to take the initiative and go talk to her.  Ask her a quick question about your surroundings (not “Do you have the time?” if you’re wearing a watch and/or have a cell phone) which allows her to either start a conversation with you or politely express her lack of interest with a short response that leaves no opportunity to keep talking.

Once she is talking with you, it’s important to keep several things in mind.  Older women have seen every gimmick and heard every line, so don’t even bother.  Don’t lie about your age or pretend that you’re older.  Some women like younger men, so be yourself and hope that the lady that caught your eye is one of these.  It may be acceptable to make a single joke about your age difference but don’t dwell on it.  Older women know that observing how men treat waiters, bartenders, and strangers is a good way to get to know their characters, so treat everyone with respect.  Don’t swear excessively or behave rudely.  It doesn’t make you look intelligent or mature.

As with any other woman, a good way to flirt with an older woman is to tease her.  Imply that you think she’s too young to drive, to drink, or to be out without her parents, etc.  Show that you appreciate her maturity by comparing her favourably to a younger woman.  She may be aware that parts of her body aren’t as firm as they used to be or that she’s starting to get crow’s feet, so she may be glad to hear that you prefer her.  Talking about your hobbies and interests allows you to show your intelligence, but don’t forget to ask about her.  Show you value her opinions and experience by asking her about something she’s knowledgeable about, a story someone’s told, or a topic you’ve been discussing.  She has lived an adult life for longer than you, so she may have a house, children, or have been married.  It’s okay to ask about these things, but be prepared to change the topic immediately if she doesn’t want to discuss them.  Acknowledge where she is in life compared to you but again, don’t dwell on it.

Physical contact is important as well.  Did she draw closer to you or pull away when you touched her back, arm, or hand?  When you ran your hand through her hair, did you catch her doing the same to her own hair (mirroring you) or make a joke about waiting to touch your hair?  

It’s good to re-evaluate your goals at some point.  Are you just having fun or are you looking to take her out or take her home?  She may just be glad of your attention and have no intention of ever seeing you again.  Or, she may be tired of playing the field and seeking to settle down in a serious relationship.  Keep these possibilities in mind and when you think the time is right, ask for her number—if she hasn’t asked for yours first.