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7 Ways to Flirt Successfully with Older Women at Work

The workplace is often a great place to meet older women who are looking for a relationship with a young stud. However, there is a fine line between successful flirting and harassment — and walking it involves knowing what works and what doesn’t.

young man flirting at work with an attractive older woman
Create that level of intimacy succesfully.

If you have your eye on a sugar mummy at work, the first thing to bear in mind is that the process is capturing her affections is a marathon — not a sprint. If you’re prepared to be patient, respectful and charming, there’s a good chance that your work relationships could turn into passionate affairs.

Granny dating at work can be a risky business, but it can be incredibly exciting if you do things right. Use these tried and tested ways of flirting with older women at work to maximise your chances of success.

#1 Don’t Limit Your Social Interaction to Just Her

It’s important that you don’t talk to the older woman you have your eye on more than you talk to other colleagues. If you’re giving her too much attention, she might think you’re coming on a little strong, or that your interest is a little obsessive.

She may also form that opinion that you’d be far to needy and clingy in a relationship. Keep your best lines for her, but make sure you take the time to chat with other colleagues too.

#2 Enjoy a Little Playful Teasing

An easy way to flirt with an older woman is to indulge in a little carefree teasing. However, it’s important that this always remains fun, and in no way belittles her confidence or self-esteem.

One way to tease an older woman involves showering her with compliments about the way she looks, or her great sense of humour. Mention that fact that she probably gets lots of offers from young men.

Pro Tip: The Power of Being Playful

There should always be an element of humour involved in playful teasing with older women at work.

#3 Promote Respectful Physical Contact

brunette mature woman about to kiss a younger coworker
Get that passionate affair you want!

Once you have established a rapport with an older woman at work, take things to the next level by instigating a little physical contact. In this respect, less is definitely more, so keep things subtle and infrequent at first.

For instance, you could gently touch her shoulder when you pass her seat in the office — a tactile way of saying “hi”. You could also reach for her arm when she’s feeling stressed or worried about something.

It is vital that you can differentiate between what is acceptable physical contact and what is an unwanted advance. Keep any contact limited to the hands, arms and shoulders.

Over time, you might be able to progress to a hug in the morning, or perhaps a brief kiss on the cheek.

#4 Shower Her with Compliments

A lot of older women will respond favourably to flirting that involves compliments. Whenever the situation is appropriate, take the opportunity to compliment her on work, her appearance or her various character traits.

However, keep compliments aimed at physical appearance to a minimum — otherwise you could come over as a little sleazy.

Pro Tip: Regarding the Compliments

Keep physical compliments related to hair, clothes and accessories. However, the best compliment during the early stages of a relationship relates to a sense of humour.

#5 Listen

Simply firing off compliments, jokes and banter won’t be enough to turn your flirting into serious interest from an older woman. You need to demonstrate that you’re capable of listening to what she has to say.

After all, it’s not all about you and your desires. When you both talk, make sure you’re taking in everything she has to say. You can show that you’re doing this by actively listening, which involves nodding, asking questions, offering advice and appropriate facial expressions.

#6 Develop Your Own Way of Communicating

If you can create an inside joke or a way of communicating that only you and she understand and relate to, flirting will be a whole lot easier. For instance, you might have a pet name for one another, or you may have singled out another colleague for some gentle teasing.

This will be something only you and she enjoy, which will create a level of intimacy that will allow you to take your flirting to the next level.

Flirting at work is a great way to get into mature dating — but you need to know how to do it successfully. By using these six tips, it shouldn’t be too long before you have the cougar of your dreams wrapped around your little finger.

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