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Dating at Midlife/how to make a first date memorable... Spoke too soon!


QUESTION: Hello. I am 40, she is 25. We have known each other for about 2 years (originally as coworkers) but really started interacting about 7-8 months ago. At first she would go out with me only if common friends would go too. Now, she is no longer in a relationship and she accepted to go out with me alone this Sunday. She gently pointed out that we would go out "as friends".

Realistically, I have kept my expectations low, even if (I'm sure) she knows I do have an interest in her. It would certainly hurt me to lose her as a friend, but at the same time, I think she is a keeper and would hate myself if I didn't give dating her a try.
We agreed to go to a pub-style restaurant. Maybe I'm giving it too much thought, but I feel that perhaps I could add an activity preferably before going to the pub, but I can't think of anything. A fancy mall is close to that place, but I think they close early on Sunday. I'm also thinking about going to our touristy downtown area instead. Basically, I want to make it memorable even if we stay as just friends. Perhaps a museum?

Any suggestions? Thankks!

ANSWER: Hi Louis,

This is such a great question.  Thank you for asking it so when I answer it online, it will benefit other midlife singles and single men in particular as well as yourself.

So, a few things to encourage you.  My late husband was 14 years older than I am.  And we did start out as friends.  Real relationships always need to have a foundation of caring friendship to last.  The caveat is, most 20 something women aren't looking seriously at 40 year old me.  So, it could take some persistence on your part.  Just keep asking her out and being her friend who she does know has a bit of a "thing" for her.  She might come round.  We are always flattered by a man just adoring us so much he sticks around.  

That said, to make this first date memorable, sweep her off of her feet just a little.  Shopping doesn't appeal to me immediately (the mall) unless it features some cool activities. If you dance whatsoever, pop in somewhere that you two could dance, even if it is just the really swanky cocktail lounge of the super cool 1940s retro hotel and dance on their mini-dance floor.  Trust me, guys her own age are not doing that.  Don't compete with them for high energy.  Be charming and a touch sophisticated.  Be a man.  25 year old males are typically still guys.  You will stand out from them.  I'm referencing the Harry Denton Starlight Room in San Francisco.  Of course you might not have that precise option where you are.  However, be inspired by that and see if you can scout out somewhere a bit more sophisticated and maybe just a little different where you live.

If there's any activity or hobby that you know she loves from having been coworkers and socializing up until now, see if there is something special you can do or place you can go where she can indulge in that activity in a more special way than usual.

Also, give her a single rose. Not red, perhaps pink.  A dozen roses and she might demure and refuse it.  A single rose is like prom.  It's just a little special without going overboard. By avoiding red, it's not too romantic in the color choice as well.   

Display gentlemanly behavior to her.  While not holding her hand because she doesn't want that yet, open the door for her, and when walking through a crowd of people, part the crowd with your should and guide her through it with a firm hand in about the middle of her back.  It's a totally appropriate touch without being too sensual for her at this time.  And it's very gentlemanly protective of her.

Dress up just a bit.  You don't have to wear a tie unless you regularly do.

What was most helpful to you?

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

QUESTION: Unfortunately, I think I spoke too soon. It turns out that 2 days before the date, she canceled it, explaining that she could not put herself in a situation she was not ready for and hoping we could still be friends. I called her and explained that I understood her position and that I did not feel offended. She said that it was her, not me, and that she was not thinking about seeing anyone else either. She went back and forth, going from perhaps considering a date in the future (just not now) to only going out with common friends. I said I understood.

Later in the afternoon I took a picture of a flower I saw at a coffee shop and sent it to her. She thanked me and reiterated that she hoped I was not mad.
I texted her saying that I was not mad, that she was my friend whom I appreciate and like and, jokingly I wrote "hmmm.... come to think of it, maybe we should go out some time" . I finished by saying that I was just kidding and that she didnt have to see me again if she didnt feel like.

Her reply was "No, I'm sorry! we can go out as friends. I just feel bad and I'm very sorry." To me, that reply sounded angry. I thought about it and my final text message said that I acknowledged her feelings, that she was ok, but that maybe we should not see each other again. I said good bye and gave her thanks for everything.
She sent two more messages asking me not to take offense, that it was not my fault, and that since she wants us to be friends she wouldn't want to ruin our friendship. I did not reply again.

We go to the same gym, where I typically see her in the morning. The following morning I did see her from the corner of my eye giving me a nasty look. as she passed by. Later on, I thought I felt her pass right behind me.
I left before her class finished. Since then, I have not spoken to her, called her or texted her.

It hurts me to see that a 2-yr old friendship has come to this, but at the same time I think I am a gentleman and I do have dignity. I don't know what made her change her mind; but if we are "friends" I don't think I deserve such discrimination from her. She did say that "nothing will happen" and I take her word for it. I really don't plan on calling her. I would like to see her texting me again, but as it is, I think our friendship is over.
I tried. Thanks.

Hi Louis,

Oh what a shame all around.  And well, yes, she is 25 years old.  So she is showing the relationship skills of a 25 year old rather than a more mature single woman in her 30s or even 40 something.  

And good for you indeed for having made the effort to pursue her when you were interested in her romantically.  I always encourage my male coaching clients to act on their attraction interest, to approach and make their romantic interests known.  "Nothing ventured, nothing gained," certainly rings true.

While it is disappointing that she not only cancelled the get together as friends, but that she made it abundantly clear that she is not ready for any kind of romantic relationship with anyone, now you know.  You both know where you stand with her as a friend where things likely have fizzled even with the friendship but also that there is no possibility for romance with her.  Clearly she has neither the interest nor the personal skills to be able to form and sustain a love relationship.

Which means, you can now turn your focus to elsewhere looking for a woman who indeed is both open to love, and a relationship specifically with you!

Many women of all ages enjoy social dancing.  Go to a dance class in your area and you'll be casually socializing with a number of women.  Then you can see if you have any interest in any of them, or just simply enjoy socializing while you look around for the quality lasting love relationship you deserve.

Dating at Midlife

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April Braswell - Dating Expert


Can certainly address the romantic questions from Boomers looking to date again after divorce or the death of their spouse. Address how dating and courtship principles remain the same, however many of the tactics are different now. How to use social media and online dating sites well which reflect your age and style, not that of your grandchildren.


As seen in Dating for Dummies, 3rd edition. I'm an internationally recognized Dating and Relationship expert, frequently on Radio and serve as "In Touch Weekly"'s go to relationship expert for questions regarding celebrity couple relationships. Additionally recognized for specifically serving the different romantic needs of the Baby Boomer generation, having contributed to such media as Gateway Media, Woman's World, and The Boston Globe.

As seen in Dating for Dummies, 3rd edition.

Smith College, BA Certifications in Influence and Persuasion Mind Body Dynamics Body Language Mastery

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