Entering thedatingpool after the midcentury mark can be daunting.

Best to test the waters a bit before making a big splash.

Im married, but I have plenty of friends trying to navigate this course.

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Your clothing choices can telegraph a lot about who you are and your confidence.

Obviously, where you are meeting and what you are doing are factors too.

Potential add-ons: A leathershoulder bagor cashmere scarf.

Tailored Wool Coat in Medium Brown; Travelers Classic Dress in Black; Sam Edelman Women’s Vienna Mid-Heel Pumps in Black; AllSaints Double Chain Link Bracelet in Gold Tone

Potential add-ons: Small drop or stud earrings, or aleopard-printscarf.

Potential add-ons: Cool shades and a baseball cap or visor.

Gap 24/7 Split-Hem Cable-Knit Sweater

Travelers Classic Dress in Black; Tailored Wool Coat in Medium Brown; AllSaints Double Chain Link Bracelet in Gold Tone; Sam Edelman Women’s Vienna Mid-Heel Pumps in Black

Embroidered Pickle Ball Bag Canvas With Monogram in Navy with Lime Stitching; Ace Tennis Skort 15.5” in Bright White