How to Attract the Woman of Your Dreams/Almost 20 year age difference


I am 40, she is early 20's.  We work together, and somewhat often talk about our nonexistent love lives.  She talks a lot more than I do.  She is a great girl, and have slowly become more and more attracted to her.  Although she is very beautiful, I am more impressed and attracted to her character, personality, spirit and mind.  I have no idea if she views me as only a friend, or "worse" a father figure and that's why she loves talking to me so much.

I recently admitted my secret crush to another woman (my age) that I dated, who surprisingly told me to go for it.  She said it was obvious that she was into me.  I was still skeptical.

Tonight, as usual, we again talked about dating, etc etc...Then she said, "You should find a young, college-aged girl..."  I didn't know what to say!!  Was this a "hint?"

We work together maybe once or twice a week (she's taking college classes, so doesn't work as much as I do), and we don't have these conversations "every" time.  But when we close together (restaurant industry) we have ample opportunity to talk and we always end up talking about dating, etc.  

Other details:  She has babysat for me before.  I have 2 kids that she volunteered to watch for free (although I did pay her anyway).  It was actually some pictures that she posted on facebook of her and my kids that was an additional clue to my other ladyfriend who told me to go for it.  There hasn't been the opportunity for any other contact outside of work recently though, and I'm not really comfortable asking at work.  

I guess my "question" is how to proceed?  Or to proceed at all?  I was very impressed with an answer you gave a 35 yo man who was attracted to his 20 yo coworker.  Should I call her?  Explain my "crush" in an email/text?  I wanna "be a man" but I'm a little hesitant (mostly because of how the age difference may be viewed by everyone else).....Any and all recommendations are appreciated!

Hello Louis!

Yes, you should "proceed". Age is only a number - even 20 years worth. People of different generations often get together and find connections despite the years. Forget how or what other people think - well, except how *I* think!  ;) It's not their life to live - it's yours.

However, you absolutely, positively DO NOT what to "out yourself" here. I know why you want to do that. It's based on a combination of not knowing anything else to do, and of hoping that she'll run the ball for you. "Oh Louis! I feel the same way..." - no, that doesn't happen in real life.

You also don't want to email or text her with any of this. Again, it just gives her far too many ways to not have to deal with it. You see her often enough that you can - and must - do this in person.

What you have to start with is to take it out of the context of work and make it purely personal. Tell her that you'd enjoy getting to know her better outside of work and tell her that you'll take her out for dinner or a drink sometime in the next week. Don't be vague here - set the date! You don't even have to call it a "date". Just plan the day of the week and time. Go pick her up (don't meet her somewhere) and don't make it a place she already hangs out.

During the, have fun. Find out about her. Get close and be sure to kiss her already! That one action turns this from being a buddy/father situation into a date. More important, it gets things moving in the right direction.

Best regards...

Dr. Dennis W. Neder
CEO/Executive Producer
BAM! Productions
Remington Publications
Producers: "BAM! TV" and “Love and Sex”
Publishers: "Being a Man in a Woman's World I, II & III”

How to Attract the Woman of Your Dreams

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Dr. Dennis W. Neder


I am the author of the books "Being a Man in a Woman`s World I & II" and "1001 Places and Techniques to Meet Great Women" and 11 others. I`ve spent the last 20 years studying the art and science of every aspect of relationships, dating and sex, and have answered over 30,000 letters from readers from all over the world. I'm able to answer literally any question regarding dating, finding and approaching women, sex, getting phone numbers, setting dates, what to do on dates, how to set them (and make sure she shows), dealing with dating problems, conversion from dates to relationships, etc. Check my website at: for much more. If your question is particularly sensitive you can email me privately and securely at:


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