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To Flirt or Not to Flirt …

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I’m in my 30’s with an adult child whose out of the house, so I’m no youngster, but I recently met a man I’m attracted to who happens to be 23 years my senior. We met via a writer’s group. Both of us have published works and neither of us were impressed with the format or quality of feedback from the group. I don’t remember how it happened, but I ended up with his contact information. After a few emails I invited him to another writers group. He accepted and has been attending, so we see each other twice a month and usually linger after the meeting to chat before heading home.

Last week I called him and asked if we could meet for lunch because I needed someone to bounce some ideas off of. He’s a wonderful conversationalist and we talked about everything, including writing. It seems we have a lot in common: gardening, love of history and linguistics, gourmet cooking, and yes, writing. We lost track of time and 2 ½ hours later we said our goodbyes.

I ruminated over the situation for a few days, then called him and invited him to dinner. Now, I’m thinking I shouldn’t have done that. I completed a public records search on him before inviting him to dinner. I wanted to know how long he’s been divorced because I didn’t want to simply be the rebound. What I found wasn’t what I expected. No divorce records, but probate. His wife died in 2009; he’s a widower.

He accepted the dinner invitation, but has never attempted to flirt with me, nor I him. I’m afraid that if I do attempt to flirt he’ll be put off because of the age difference. I don’t want to make him uncomfortable, nor do I want to be seen as a gold-digger or as having an Oedipus complex.

I feel like dating is a mine field. I’m flustered and unsure of how, or even if, to proceed. It’s always been me who initiates contact. I invited him to the other writers group; he accepted. I invited him to lunch; he accepted. I invited him to dinner; he accepted. Is this a red flag? If he were actually interested in me, wouldn’t it be the other way around? What about the taboos regarding dating older men? I don’t want to be seen as seeking a father figure.

To Flirt or Not to Flirt …

Answered by on -


 Good friends who share our interests and delight in the same things are hard to find — even harder to find as we grow older. Why not treasure this developing friendship? It doesn’t need to turn into a “dating” situation.

It may or may not lead to something else. The most stable relationships are those in which the two people are very good friends. If the friendship doesn’t lead to romance, you will still have added an important friend to your life. If it does evolve into romantic love, that’s a bonus.

In the meantime, please stop keeping score about who initiates contact. He may be shy. He may not know how to ask you to do things without implying more than he is ready for. His wife may have been the person who always organized social events so he’s out of practice. It really doesn’t matter. What counts is whether you enjoy each other’s company.

I wish you well.
Dr. Marie

To Flirt or Not to Flirt …

Therapists live, online right now, from BetterHelp:

Dr. Marie Hartwell-Walker

Dr. Marie is licensed as both a psychologist and marriage and family counselor. She specializes in couples and family therapy and parent education. Follow her on Facebook or Twitter.

APA Reference
Hartwell-Walker, D. (2018). To Flirt or Not to Flirt …. Psych Central. Retrieved on August 6, 2020, from
Scientifically Reviewed
Last updated: 8 May 2018 (Originally: 22 Jul 2016)
Last reviewed: By a member of our scientific advisory board on 8 May 2018
Published on Psych All rights reserved.