19 March 2014

how to go on a dinner date when you're 50ish

A girlfriend of mine has a dinner date tonight. Late last night she texted me in a panic wanting some advice about what to wear, what to talk about, what to do when the check comes etc. And I thought about love/romance/dating while I was making coffee this morning and came up with a quick guide for what I think is the perfect first dinner date when you're 50ish and it turned out so well I decided to share it for the benefit of other friends who are back in the dating game after maybe decades of being married or happily single. The way I see it - the only two things to think about for the first dinner date are 1) what to wear and 2) what to talk about.

wear something understated that's already in your closet that you feel comfortable in. going shopping for a dinner date that may be over before the appetizer arrives is simply a waste of your money & time. if the dinner date is a go then you can start to get excited about what you're going to wear on the first date.

talk if you've actually been able to find a man who's actually asked you out for a dinner date - this means you've actually had a few actual face-to-face conversations with him and talk should come easy because really past 50 would you be willing to waste an evening on someone you haven't actually met right I didn't think so. but talk over dinner can be tricky and i think it's probably best to take along a little cheat sheet so you don't get off track. 

cheat sheet 

  1. present & future tense verbs only if you stick to talking about the present and the future you will eliminate any possibility of bringing up painful subjects from the past like ex-wives/husbands, extra-marital affairs, back taxes, student loans, jail time etc and you will force yourself to focus on the you you are in the process of becoming.
  2. body language i think the first dinner date is a fact-finding mission for figuring out if this is someone you like enough to have dinner with again - so for God's sake don't flirt, play with your hair, cross your legs too much, think about soul mates or happily-ever-afters because you see where that got you before right - especially don't pay particular attention to his hands or lips etc. focus on your present & future tense verbs only and on you and your happily ever after and you won't go wrong.
  3. the check if he's invited you out for a dinner date he's going to pick up the check so don't do that who's going to pick up the check shuffle when the check comes. if you don't have a lot of practice in letting men pick up the check here's what you do. when you see the waiter about to come over with the check simply excuse yourself to the bathroom and by the time you've updated your best friends via text message on how the dinner date is going and get back to the table it'll all be over and you'll be ready to go.
  4. nightcap no nightcap on the first dinner date. unless it's raining and you're in paris or new orleans or new york and there's a new morning or a blue note or a snug harbor conveniently located around the corner and if you decide to go that route - you're on your own gf.
  5. ride insisting on meeting a man at a restaurant on the first dinner date i think is the single most important step to take if you're considering changing your facebook status from single to "it's complicated" or "in a relationship." you are not in high school anymore. you are not getting picked up to go to the prom. insisting on showing up in your ride will eliminate any questions about what if anything is going to happen after dessert. having the keys to your ride at all times during the evening says i know who i am, where i live, where i'm going, and especially says i know who's taking me home.
  6. goodnight kiss yes. Beside your car. Like high school. Then just go home. Alone. You have to trust me on this one.

So for my friend [let's call her Rachel because I don't want to embarrass her] I really had a good time putting this how-to together because it's forced me to think about maybe saying yes to a dinner date sometime in the next few years :) !!! And for my facebook friends and readers - while I know a lot about dating - I don't know everything and so would love it if you put in your two cents here in the comments x

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