Expert: Aaron Beck - 9/27/2006

Question
My name is Paul. I am 35 years old and live in Orlando, Florida. There is a 20 year old woman at work that I have been exchanging words and mild affections with. We have discussed the fact that there is a bond between us, but really haven't given it much more conversation. We spent some time talking and laughing one time out of work at her place, nothing happened. I feel because of the considerable age difference there lyes hesitation on both parts to move closer, or to expose conversation that will set it completely apart. I am attracted to more than her physical, I am attracted to her energy and intelligence level, I'm just not sure if I should get my hopes up too high and continue persuing her...Paul

Answer
My name is Paul. I am 35 years old and live in Orlando, Florida. There is a 20 year old woman at work that I have been exchanging words and mild affections with. We have discussed the fact that there is a bond between us, but really haven't given it much more conversation. We spent some time talking and laughing one time out of work at her place, nothing happened. I feel because of the considerable age difference there lies hesitation on both parts to move closer, or to expose conversation that will set it completely apart. I am attracted to more than her physical, I am attracted to her energy and intelligence level, I'm just not sure if I should get my hopes up too high and continue perusing her...Paul


Paul,

I have your question her and I will do my best to add some insight to the situation.  

First a couple of quick observations.  Since you work with this woman, you have to ask yourself how stable is she?  If you do make a move on her is she likely to scream “Sexual harassment!” and compromise your job?  Even if you think she is not that type person now, could she be that type if the relationship goes bad?  You have the double whammy of her being younger (i.e. possibly less stable) and of working with her.  Anyway, not trying to talk you out of it but at least consider those scenarios.

As far as the situation itself, I don’t see any problems at all and I definitely don’t think that you are unrealistic in wanting to go out with her.  It happens all the time.  As a general rule, until you hit about 40 or so ALL women will still consider you “in the window”.  Women are different than men in that regard as you probably know but if you don’t know, I’m telling you.  The last woman I went out with was 20 years younger than me and it was more an issue for me than her.

Alright as far as the specific dynamic of making something happen.  You are absolutely going to have to make the first move.  Men have to make the first move anyway but it’s especially relevant in your situation because of the age difference.  Possibly one of thee reasons she is (or might be) attracted to you in the first place is she is looking up to you as a more mature person.  Women look to men for leadership and it’s especially so here.  

Here’s how I’d do it.

Paul: So Karen, how come someone as attractive as you isn’t dating someone? (stop talking)

This is actually a pretty good opener because it’s non-threatening and it’s “normal” question.  You have also included the fact that she’s “attractive”.  Her answer can be revealing all in itself but no matter what she says you’re going to follow it with

Karen: XXX

Paul: It just seems a shame, you’re young and beautiful (note the upgrade), you have a lot of energy and you seem to have so much going for you.  

She will take this as a huge compliment.

Here’s where you want to listen carefully for something to build on.  As a minimum, you have opened the door for male-female talk which is always fertile ground.  What you are listening for is some opportunity to introduce the age issue (if you want some assurance on that front).  If she says anything that includes the words: immature, crazy, boring,  etc. when referring to men her own age, you’re golden.  She has given tacit approval to move in.  

You do not want to say anything like, “I wish I was 15 years younger” or “what’s the oldest guy you’ve dated?” because those are “fishing” lines and you are passing the decision making process over to her and she doesn’t want that.  Women want to be led (i.e. seduced).

The more intimate the setting for this conversation the better.  If you could get back to her apartment, that would be the best place.  Based on the results of the conversation, you’ll have to make your decision as to whether to go ahead or not.  I don’t think you should “ask her out” in the traditional sense of the word (i.e. public restaurant etc.) because you will call attention to the age difference as the other couples will be more age-similar, the best thing would be dinner at either her place or yours.  That will give you approximately six hours together and there will be a lot of interaction, if it’s going to happen, it will.

Alcohol can also help but a MINIMUM amount.  Minimum means two glasses of wine apiece (i.e. split a bottle of wine).  You are probably looking for some more assurance that you won’t be rebuffed -- which is normal -- but I don’t usually advise guys to worry about that, I tell them, “It’s not up to her if you like her or not” but in your case, I can understand that you want to be on firmer ground before you move ahead.

To recap, you have to make the first move and age is not an issue.

Hope that helps, let me know how it works out.

AB