At 65, What Do I Wear on a First Dinner Date?

Dress Your Feminine Best for a First Dinner Date at Any Age

Dress Your Feminine Best for a First Dinner Date at Any Age

Hi Ronnie The Dating Coach,

I have a very important question. I am 65, a widow and just starting to date. I recently met a man through J-date and we played bridge together one afternoon. It was a delightful and I really liked him.

Now, he asked me out for our first dinner date! So, here is the question… What do I wear? My single friends say I need a dress, but I don’t have one. Advice, please. And is there any other important etiquette I should keep in mind?

Waiting your response…Elisabeth


Der Elisabeth,

I agree with your friends. Most men like a feminine woman. So a dress or skirt are good choices for a first dinner date. If you don’t have any and don’t want to buy one right now, then wear a feminine top with pants. Men notice shoes too. Do you have any nice shoes?  Heels (they don’t have to be very high) or strappy sandals?

Then just be yourself and stay on positive topics. No negativity and or sad subjects. And you probably know this but don’t talk about your husband either. That’s like bringing him on your date with you – a big “no no”. If your date asks about him, give him a brief answer, then move on to lighter topics.

 You want to be your most delightful self – showing him your happy, fun side. But don’t worry – you can be yourself – but your BEST SELF.

Dating is like interviewing for a job. You wouldn’t talk about how bad the job market is, how you hate your boss, how interviewers are cruel, how there is age discrimination, etc. You get the idea.

And if your date goes to the dark side conversationally, see what you can do to shift the conversation and lighten him up. Sometimes men need this too.

Men chose women who are fun to be with and make them feel good and masculine. They want to be proud to be with you. That’s it!

Lastly, don’t put too much pressure on one date. Remember your first dinner date is still a get-to-know-you event. Too much pressure can really get in the way of a good time. Remember – it’s just ONE date.

After this date, make it your business to get some dating clothing and no excuses! Buy a few outfits that you feel really
good in – this is so important for your confidence and your femininity. When you look good, you are so much freer to be your best self. That’s the woman who will captivate a man for sure. And if not this man, there are plenty more fish in the sea for you to dazzle.

Enjoy your first dinner date!

Wishing  you love,



Photo Credit: Aroid



Single for too long, Ronnie wanted to find love. She put her skills from personal development and her spiritual path to work, dating 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to manifesting and midlife dating, she founded It’s Never Too Late to help smart, successful women find love or live an empowered and magical life. Ronnie Ann Ryan, MBA, CCC, is a Certified Coach who has helped 1,000s of midlife women with her Love & Magical Life Coach services. She’s the host of the Breathe Love & Magic podcast and has been featured on NBC, ABC, & Fox News, NPR, BBC, eHarmony,, and Connecticut Magazine among others. Also, Ronnie is the author of 6 books which are available on Amazon.

2 thoughts on “At 65, What Do I Wear on a First Dinner Date?”

  1. Your advice sound good ,But this outfit on the picture looks more appropriate for going to church ,on Easter Sunday than for a dinner date .Hats are for church or receptions not for a first date .
    And that light fabric dress call for a girdle or at least tummy control panty .And those sensible shoes are just a turn off .
    Dress like this Elisabeth will look ten years older ,just like a sweet granny .
    I ll suggest a tailor suit ,40′ s style,straight skirt ,back slit ,short jacket . ( check todays news girdle ,like nude control.
    body suit if you need it ,and a good bra) ,the suit must be light grey or black ,I dark grey ,underneath a lace blouse ,V neck ,or a bodysuitv,in bright color or pastel .what ever suit you .Your shoes ,( with pantyhose mandatory for a dinner ,no bare legs past 50 ) Shoes have to have a bit of heels,low or high ,but skinny heels .And not cover too much the feet .Do not match your shoes with your purse or belt .Black shoes is the sexier .Many woman over 50 wear hair too short ,its more sexy if it just at the shoulder .If your hair is short ,check latest high fashion like vogue magazine for idea .zig its long check today summer 2012 modern updo .
    Check 40′ fashion style ,and add modern shoes ,modern blouse ,modern hair doe and minimalist jewelery .Tiny Pearl is good but nothing on your lapel ,nothing oversize .Not much make up but no bareface .
    Voila .
    Have fun Elisabeth and dont worry about what you say ,just let him talk ! Listen ! Or talk about current event but no religion ,no politic ,no past relationship on the first date .


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