She Asks Delilah Should I Ask An Older Man Out

What is Delilah's Advice To A 25 Year Old

July 7, 2018
Delilah Dilemma

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This Delilah Dilemma is from a young woman of 25, crushing on a man who was nearly 20 years her senior.  And I was there with you for the entire letter until I get to the, “ Should I ask him out?”

Carla, He's a grown man…. right?  And he knows you're interested, that you’ve been flirting, (you said you caught him looking at you.)  If he wants to pursue a relationship with you, he needs to let you know that. There is certainly nothing wrong with saying “let’s get together and talk, to have coffee after work sometime” , but if he is interested in a relationship, let him pursue you.  I know that sounds old fashioned.  The age difference doesn’t matter.  You are over the age of 21 or 22.  You may be in different places in life and that may matter to him.  I'm sure since he is a mature man, that age doesn't matter.  But sometimes when there's that big of an age difference, you’re at different places in  life.  If you are 25 and you have never been married, you might want the white dress, you might want the big events you might want Kids, you might want a lot of things and he's 20 years older. He may have already been there, done that, and not be the least bit interested in going there again.  So, it’s not so much an age difference as it is a place in life difference.  Most people that I know that have a large age difference in their relationship are very happy, but they have to work through a lot of issues when they are at a different place in life.  But here, the issue is he’s been checking you out and if you guys have lots of good conversations, then he needs to pursue you can. And Yes, letting him know that that is a possibility might be a good thing but don't be too available when people are too available other people lose interest, Do you know what I mean by that?  Let him realize you are worth a little bit of effort. -D