Midlife Woman's Dating Toolbox

So you’ve found yourself back in the dating world after a decade or two hiatus and you feel like you’ve been dropped off in the middle of another universe, right?   I felt very much the same not so long ago, but now that I have a few tools in my dating toolbox, I thought maybe you’d like to add them to yours.  

I am slowly figuring this thing out and by no means have all the answers from the 20+  first dates I’ve been on post-divorce.  Even though I’ve taken a few stabs at a relationship, most were “first-date-only” and I've learned a lot!  All of these meetings taught me some valuable things about myself and dating.  So, I share with you some tried and true tools from the field:

1-Thick Skin:  Dating at mid-life is not for the weak of heart.  When you first start dating (online, or otherwise), remember not to take things personally.  All of us have non-negotiables, which can be anything from smoking, to ex-cheaters, to tattoos, to someone who wears clogs (Ok but seriously, at our age, who wants to be seen with that?)  If we are truly being ourselves, then it’s okay when someone finds out we have one of the non-negotiables on their list.  It says nothing about us as a person, it is just a preference.  Shake it off, don’t go changing and move on to the next!   

2-Flirting Button:  When you’re married, you probably turned off your man-radar and flirting skills without even knowing it.  Over the years, You forget how to talk to men in a non-sterile way, so make sure your flirtability is turned back on and start using it!  Smile at men when they look at you, look out and around, say hi, wink if you’re a winker!  Then, if you want to talk to someone, try bumping into his cart, or if you are really bold and flirty, try asking his opinion on shaving cream!  Feel good about yourself when you leave the house and you will effortlessly attract the attention of others. 

3-Smart Phone:  Okay Ladies, time to up your technology ante!  It’s fairly mandatory in today’s world if you want to have any social life, dating or otherwise, you need a smart phone.  Texting is a huge part of modern relationships, so you need to get text-friendly, know how to take a decent ‘selfie”, and have friends take good pics of you doing activities you enjoy so you can share them right from your phone.  There are also loads of great dating apps to make dating fun at your fingertips!    

4-Honesty:   Unfortunately, many people our age are still trying to play games but I find if I’m honest, I tend to attract people who are honest.  I had a single friend who never got asked on a second date.  While trying to help her figure out why, she showed me her online profile pictures, which honestly weren’t a very genuine likeness of her.  So fess up, whether you’re a BBW, very tall, you smoke, like to party, wear glasses, collect PEZ dispensers, whatever the case may be, just be upfront.  I tell men my height, I never wear flat shoes and I’m a size 14.   I can’t imagine how awkward it would be to sit across from a man who had failed to mention his picture was 10 years old, 40 pounds and 17 wrinkles ago, etc.  I don’t want to be either person in that scenario!

5-Lingerie:  I am NOT saying that a first date should ever see your lingerie, but you know it’s true, ladies, when you have on sexy lingerie, you just feel more confident and sensual (yes, even if it’s not comfortable.)  The morning my ex-husband moved out, I threw out all of my lingerie and have enjoyed building a whole new trousseau.  Try something daring, too, go for things you haven’t worn before.  I did and I had no idea I’d be infatuated with thigh high nylons!  Confidence is Sexy and its okay if some of it comes from a pair of black lace panties!

6-Google/LinkedIn:  I’m not ashamed to admit I have googled almost every date I’ve been on.  There are plenty of “playa’s” out there and I don’t have time for that nonsense!  My BFF and I have gotten quite good at our detective work, but my favorite validation is when I find them on LinkedIn.  I feel if I can verify what they’ve told me about their professional life, then that’s good enough for me.  After you get to the date, it’s all about instincts, so trust yourself the most!

7-Boundaries:  This may come as a shock to you, but there are plenty of men our age who want sex on the first date.  Actually, most expect it by the third and if you don’t, you might just never hear from him again.  Shocking, right?  So, I look for a way to let them know my boundaries before we meet so their expectations line up with mine.  My mantra is “first date/first base.”   I am willing to kiss someone on a first date if I like them (because frankly, kissing is one of the best things EVER), but I make it clear there will be nothing more, unless they want a knee where it doesn’t go!

8-Your own car:  Always plan your own escape if you need it…get-away cars are not ONLY for criminals!  I just prefer to meet my date in a public place until I feel safe, in fact, only 3 men have been to my home.  Ladies, always make him come to your part of town for the first date…you’re worth it!

9-Safety Friend:  This might be the MOST important item on the list!  My BFF is mine and before any date, I send her his full name, his phone number, meeting place, and start time because as they say, ”safety first.”  So, thirty minutes into every first date, she sends me a text.  If I already know it’s a great time, then I reply “I’m great and text you after.”  If I’m still on the fence, I let her know to check back in another half hour, or if it’s not going well at all, I can ask her to call me with a diversion (the kids are running with scissors, the dog is puking, she broke her big toe, etc!).  If I ever needed a big rescue, I have no doubt she would grab her husband or sister, show up and help a girlfriend out!   In fact, she’s been known to do a drive-by just because she thinks it’s fun!  Gotta love a gal-pal like mine, and no I’m not sharing!

10-Wallet:  You should always offer to pay for the date.  Now, I never have because men of our generation tend to be fairly traditional but I like to offer.  You should definitely pay for some subsequent dates, so be prepared.   I have read about women who pay if the date is bad on matter of principal alone, this is generally a sign to the man that he won’t be getting a second date, but I think this is backwards thinking.  If my date was that bad, I would order the most expensive item on the menu and NOT offer to pay, but whatever. 

11-Disposable Toothbrush: These little things are the best…tiny, minty, disposable, discreet objects of fresh breath goodness!  If you WANT him to kiss you goodnight, sneak away for a quick brush and then, enjoy that worry-free first kiss!   

12-Gum and Handbags: But what if you DON’T want him to kiss you?  Put a piece of gum in your mouth.  Also, holding your purse in front of you as you walk to the car can be a girls’ secret weapon.  Most men aren’t into gum swapping or being hit over the head by handbags and will get these not-so-subtle hints!

Regardless of what you put in your toolbox, remember to be open, genuine and have fun.  Stretch yourself, look for life lessons and embrace all of the wonderful new things this chapter of life has to offer you.  And then meet your best friend for drinks afterward and dish out all the details.   You will either swoon like school girls at new possibilities, or double over laughing if it was a comedy of dating errors.  Either way, you can’t lose!