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Women Dating Over 40, 50, 60: Great First Impressions

by Raymond Gregoire (Mr. Boomerina)

If you’re widowed or divorced and you’re a baby boomer, you might not have dated in 20 or 30 years, but even if it hasn’t been that long, starting to date again can be a terrifying experience. However, it does not have to be.

how to dress for a dateHey, I’m a guy and I’ll tell you what guys are looking for, at least what I was looking for when I started dating after the death of my wife to whom I had been married for 38 years.

How to Make a Good First Impression:

The old saying goes, “You only have one chance to make a good first impression,” so don’t blow it. I did most of my dating through match.com and being visual, as most men are, I relied on the pictures the women posted. Well, it soon became obvious that the pictures they posted were often 15 years old and did not reflect their current appearance. Call me shallow, but the use of an old picture versus the real person who showed up for our coffee date never resulted in a second date, because it indicated basic dishonesty, making me wonder what else they were fudging about.

Tina Boomerina, the gal I eventually married, had a good online photo but she was even more attractive than her picture. I think it’s better to underplay your appearance and surprise your date than to overplay and disappoint.

White Teeth:

Well, I want to point out what I noticed next with first dates. For me, it was the woman’s smile. So, it is important that you have your teeth whitened, and if you have the money, have any defects like a crooked tooth or a gap corrected.

Get Some Good Outfits:

You should invest in a few good outfits and throw away your Wal-Mart and Target clothing. New clothes and a great smile will be the best investments you will ever make when it comes to dating. Also, wear good accessories, such as costume jewelry, to give you that extra quality that sets you apart. In Tina’s case, it was her custom style, her hat.

Update Your Grooming:

Spend a few dollars to have your hair colored and cut by a pro, not Supercuts or HairMasters, and get your nails done. Good makeup is also a must, not Cover Girl but higher-end makeup, as you get what you pay for. The right makeup can take years off your face for a small fraction of what you could spend for a facelift.

Does it work? Well, when Tina walked into Starbucks on Sept 12, 2004, I think I instantly fell in love with her and we married 9 months later.

Other things to do are: keep good eye contact, don’t complain about your former husband, be positive, and by all means, try to center the conversation around your date’s interests.

Many of Tina’s articles found below will fill in the “how tos” of getting the right look for your body type.

More Articles for Baby Boomer Women Over 50 or 60:

How to Look Better in Online Dating Photos: 11 Tips

Fashion Tips for Pear-Shaped Women: From Real Women

Apple Shape Women: 31 Rules for Your Body Type

Boho Jewelry: 6 Big Styles for Plus Size Women

Tina Boomerina (AKA Christina Gregoire) is a Baby Boomer born at the end of 1952. Her mission is to make the internet a kinder and gentler place for Baby Boomer women around the world. Tina's specialty is fashion for women over 50.

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  1. brittany griffin

    What brand is the green jacket on the first page????