General Dating Questions/Younger Girl

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Question
QUESTION: Hello:

I used to work with a much younger girl at my place of employment.  She no longer is employed there but during her employment I became attracted to her.  I am 40 years older than she is.  I am 61; she is 22. I keep asking myself whether or not I should have taken a chance and asked her out or get together after work or on a weekend.  I did not because of the large difference in our ages.

1. Do you think that I should have taken a chance and asked her for a date?  I keep kicking myself for not doing so.

2. Should I contact her and let her know that I wished that I would have asked her out?

I thank you for your reply and advice!

ANSWER: Hello Kenneth!

1. I don't know enough about the situation to say specifically. In general I recommend that someone takes a chance. However, considering the various problems that I know of here (age, having worked together and thus, having common contacts, etc.) and the ones I don't, I'd say you are probably better off not having gone for it.

With that said, there's nothing wrong with putting out feelers to try to gauge a level of interest. For instance, saying, "Yeah, I usually hang out at [bar]. If you're good, maybe I'll tell them to let you in some day". The point here isn't to directly ask for a date as much as to gauge any interest.

2. No, you shouldn't. You didn't mention how long it's been since she left your employer, but without some other context, contacting her now might be somewhat creepy.

Regards...

Dr. Dennis W. Neder
CEO/Executive Producer
~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.
BAM! Productions
Remington Publications
323.638.4145
http://beingaman.com
Producers: "BAM! TV" and “Love and Sex”
Publishers: "Being a Man in a Woman's World I, II & III”


---------- FOLLOW-UP ----------

QUESTION: Hello Dr. Neder:

I want to thank you for the reply.  The person that I am referring to in my first question is a student.  She left her job to finish her degree outside of the university.  I am thinking about sending her a graduation card with a note congratulating her for graduating.

I had wanted to include the following in the note:

I was instantly moonstruck by your charming personality, beauty and pretty smile when I first met you.  I just wish that there were not such a large age difference between us! I certainly would have liked to get to know you better, but that’s the way life is at times.
-or-
I certainly would have liked to have started a closer relationship with you, but that's the way life is at times.

The above is just a part of the message not my entire written comments that I would include.

Do you think that it is appropriate?

And also, can you please make your reply private?  The option is not available from my end.

I thank you for your follow-up reply.

ANSWER: Hello again Kenneth!

Send the card if you like, but DO NOT include that text!

What you're trying to do is to get her to do all your work for you. You want to open the option by indicating some interest and then have her swoon all over you. It won't work. It's not her job to do that and she damn-well knows it.

If you want to congratulate her on the accomplishment then make that the context and message. If she responds you might have an option to then offer to celebrate over a drink or something. Making your interest in her the impetus for the congratulations (and in fact, coming out like this in general) is creepy.

Unfortunately, no, I can't make a question a user asks private if they don't start it as such.

Regards...

Dr. Dennis W. Neder
CEO/Executive Producer
~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.
BAM! Productions
Remington Publications
323.638.4145
http://beingaman.com
Producers: "BAM! TV" and “Love and Sex”
Publishers: "Being a Man in a Woman's World I, II & III”

---------- FOLLOW-UP ----------

QUESTION: Hello Dr. Neder:

If I changed the above text to the following: "I miss your charming personality and pretty smile."  Would this be creepy or make her feel uncomfortable?


I thank you for your reply.

Answer
Hey Kenneth!

You need to ask yourself, "What do I hope as an outcome by using flirtatious, inciting language?" She'll ask the same thing, and yes, I know that's your goal.

Ultimately, you want her to swoon all over you. ("Oh, Kenneth!!...") but that simply doesn't happen. There's too much distance here and if you want to make something happen, you're going to need to be more direct without being overt.

Regards...

Dr. Dennis W. Neder
CEO/Executive Producer
~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.
BAM! Productions
Remington Publications
323.638.4145
http://beingaman.com
Producers: "BAM! TV" and “Love and Sex”
Publishers: "Being a Man in a Woman's World I, II & III”

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Dr. Dennis W. Neder

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I'm able to answer any sort of question related to the approach, meeting people, dating, sex, relationships, break-ups, non-legal marriage and divorce questions, and anything in between. I've helped over 30,000 people with their individual issues. IMPORTANT: Please, PLEASE don't ask me, "what was he thinking..." or "why did he say..." types of questions! I DO NOT READ MINDS! There are 1,001 reasons why someone does what they do, says what they say or thinks what they think. If you *REALLY* want to know what they were thinking, saying or why they were acting that way - go ask them! Be sure to check out my FAQ's on my website at: http://beingaman.com. You can email me directly at: dwneder@beingaman.com.

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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, and have answered over 30,000 letters from readers all over the world. My main focus is men`s relationships with women, but I also have many female readers and answer questions for them regularly as well.

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Doctor of Philosophy

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