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How should I flirt with a co-worker who is twice my age?

Tagged as: Age differences, Crushes<< Previous question   Next question >>
Question - (14 April 2012) 3 Answers - (Newest, 14 April 2012)
A male United States age 36-40, *rymsoul writes:

Ok, well there's this mature lady who works at the same company as me. In my opinion, she is sexy as hell. She's a bit more than twice my age. Infact, her son, who I knew personally is three years older than me. INFACT, her son has two kids, which technically makes her a grandma. I know it sounds creepy just hearing it but trust me when I say, she isn't your typical grandmother. She looks like she could pass for 30 and she gives the younder girls a run for their money in physical attractiveness. I've had the biggest crush on her since we started workig together. We've gotten friendly to the point where we hug regulary and talk about stuff, but I obviously want more.

My question to you guys is, how do I flirt with a mature lady? Is it the same way with flirting with girls around my age? Should I ask her to the movies, lol, or is that a bit. . .childish considering the circumstances? I honestly don't know if we could ever be a serious couple but I know I have a strong physical attraction to her. What can I do?

View related questions: co-worker, crush, flirt, grandmother, money

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A female reader, natasia United Kingdom +, writes (14 April 2012):

natasia agony auntYou should treat her exactly the same as you would any woman you like. Absolutely. By my calcs, she is in her early 40s, so all she is is a more experienced, slightly more world-weary version of a 20 year old woman. No different. It is quite possible to be 42 and pass for a 28 year old. I personally gave birth to my youngest child a day after I turned 40, and then went to Sainsburys a couple of weeks later and ... they would not sell me a bottle of whisky. I am not joking. TWO of them wouldn't do it. They wouldn't believe I was older than 21.!!!!!!! In the end, an old guy came up - in his 70s - and said 'what are you two idiots playing at?' ... me and all the other customers in the queue were crying with laughter. When I said I was born in 1968, the guy on the counter thought I was taking the pxss in a very big way, and called his supervisor. They were ready to prosecute me ; )

So, I know it is totally possible to seem 20 even and be 40. I feel mostly about 15, and quite a lot about 7 years old. I guess it works ; )

So please don't think you have to approach her any differently. She is not different. She has just been alive longer. That is all.

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A female reader, YouWish United States +, writes (14 April 2012):

YouWish agony auntWhatever you do, don't call her a hot grandma or say anything that highlights the age difference!

Other than that, she might think that you'd never be interested in her, so all you've gotta do is ask her out! Before you do, think about what she's interested in. You've spent time talking to her, so you know what she's into.

Ask her to the movies if she's into them, but you'll be head and shoulders ahead if you can think of something she really likes to do. That shows thought. Dinner out is always great, of course. Is she into concerts, or the nightlife scene, or is she into quiet things like art museums, or is she active and into biking, skiing, or is she adventurous?

Trust me, it's not creepy that you're attracted to her!

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A female reader, janniepeg Canada +, writes (14 April 2012):

janniepeg agony auntYou will both feel somewhat uncomfortable about this so the way to do it is to act like age is just a number. It's impractical to tell you to act like a 50 year old but just don't be boyish. You can do that. You are hugging and stuff but doesn't mean she wants more. You can ask her but be prepared to hear that she just wants to flirt but nothing more. It's better to know her intentions before treating her to a movie. The only difference between a 50 year old and a 20 year old is that you can be more direct to an older pereson while with a younger girl you need to be more tactful and go slow.

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