Navigating First Dates After 50: Tips to Boost Confidence and Find Love

Dating over 50 can be intimidating—but it doesn't have to be. Here are tips for planning for your next first date.
Couple eating dessert in fancy restaurant

If you’re over fifty, chances are you’ve had some bad experiences with dating and have been on a lot of first dates. Trust me; I’ve been on more than you could count. First dates can be nerve-wracking and awkward—especially if it’s been decades since you’ve last had one. Once you get the hang of it, though, going on a first date can be a major confidence booster. And, dare I say, fun! Remember the thrill of first dates in your twenties—well, the thrill is still out there. So, while dating over 50 can be slightly different than it was back then, with the right game plan, you can avoid some common pitfalls and anxieties and actually enjoy yourself.

Know What You Want

Elderly couple in love hugging on Valentine's day. A loving senior husband gives his wife a tender bouquet of tulip flowers

It will save time! Are you looking for companionship, a long-term relationship, or a roll in the hay (wink wink)? Do you want something casual or serious? What features are you looking for in a man? Now, cut that list in half and ask yourself, what are you realistically looking for in a man? And what are your non-negotiables?

Let Go of the Past

At our age, we all have baggage. But that was then, and this is now. Don’t dwell on what went wrong with your last relationship. It will only mess with your head. You’ve learned lessons. Now move forward and use what you’ve learned.

Don’t Stress

A bit of nerves on a first date is natural—in fact, those butterflies are half the fun. But the more relaxed you feel before your date, the more relaxed you’ll be during it. Do whatever it takes ahead of time to put yourself at ease.

Keep it Simple

If you are on the anxious side, keeping dates short and sweet is always a safe bet. Try going for a coffee or a hike. If things go well, that coffee could extend to drinks, or you could hike all the way to dinner. After all, we ladies love a spontaneous man.

Dress Comfortably but Appropriately

Smiling couple talking at table. Happy man and woman are in casuals. They are spending leisure time in restaurant.

A good first-date outfit should make you feel like a goddess and reflect who you are. Try to dress comfortably. Don’t wear anything so tight that it will constrict your breathing. Wear something nice, but not too nice. Don’t show up for a coffee date looking like you’re going to the opera. Dress appropriately for the occasion, and remember that what you wear will communicate things to your date. If you show up in sweats, for example, he’ll know you don’t care very much about how you look. 

Safety First

Get his first and last name. If you can, vet him on the internet or social media. Tell a friend where you’re going, what time, and with whom—especially if you met him online. Have an exit strategy in case things go south. Don’t get in the car with him. And never ever ever go home with, or bring home a stranger on a first date. 

Keep an Open Mind

Sure, your ex-husband is a jerk, but that doesn’t mean every man is a jerk. Please leave the jaded attitude at home and give the poor guy a chance. Have the actual date before you decide he’s not the man for you. You never know. His humor, style, attitude, or looks could win you over if you keep an open mind and give it a little time.

Be Yourself

The most important piece of advice is to be your absolute best you. Never make yourself out as someone other than who you are to attract a man. If he thinks you’re all silly giggles and bubbles, and he’s into that sort of thing, he won’t be too happy when he later discovers you are intense and intelligent. Be honest. Don’t try to impress a first date by pretending you are into things that are important to him. Being unapologetically yourself will go miles with men who are tired of the phonies. Assume he wants someone real—and that it is the real you.

Always be Prepared

If you are meeting at a restaurant, look at the menu beforehand. We’ve all been caught in that Can I take your order?” freeze when we’ve been talking instead of reading. Just in case, having some conversation starters on hand is a good idea. Do a bit of social media sleuthing to find out some of his interests. Keep your topics light. Think about some interesting questions you can ask and some answers to the questions that may get volleyed back to you.  

Stay Away from Controversial Topics

First dates are meant to be breezy and fun. They’re a window of time wherein you get to know him with playful banter and witty repartee. They are not the time to ask him about his political views, why his last relationship ended, or your future together. You may want to know about his finances and religion, but now is not the time to ask. While certain serious topics may be important to you, let them roll out organically, over time, in the course of authentic, natural conversation.

Don’t be Negative

Passionate, couple, talk, restaurant, table.

Life is hard. We’ve all had our challenges. He doesn’t need to hear about yours on the first date. He doesn’t need to hear how your ex cheated on you, how your horrible boss doesn’t appreciate you, or the blow-by-blow of the death of your beloved cat. First-date conversations should be upbeat and positive.  So, for the love of God, leave your money woes and your online horror stories at home. 

Save Grilling for the Barbecue

You want to get to know him, and, let’s face it; men love talking about themselves. But let him ask questions as well. And don’t drill him. You are on a date. Go for a dialogue, not an inquisition.

Listen Thoughtfully

Don’t talk over him, don’t interrupt, and don’t think about what you’re going to say next when he’s in the middle of a sentence. Just look him in the eye, humble yourself, and really hear what he’s saying. If he does the same for you in kind, he’s a winner.

Be Good

Don’t get drunk.

Enough said!

Watch out for Red Flags

He drinks too much, pressures you to return to his place, forgets his wallet, and you have to pay the bill. If he shows you any sort of questionable, addictive, or aggressive behavior on a first date, then run for the hills.

Mind Your Manners

Please and thank yous. Napkin in your lap. Don’t talk with your mouth full. And for the love of God, put down the phone! 

Saying Good-Bye

It’s that awkward moment at the end of a date that most first-daters dread. To kiss or not to kiss? Everyone has their own rules. Always stay within your comfort zone. If he moves in to kiss you and you’re not feeling it, reroute to a hug. But if you want that first kiss, body langue is always a good tell: smile, play with your hair, lean in his direction…And remember, if you’re blabbing at 60 miles an hour, you’re not giving the guy a chance. Slow down, shut up, and savor the moment.  

Follow Up

A successful first date doesn’t end with a goodnight kiss. If you like him, text him to thank him and say what a great time you had. Don’t get annoyed if you don’t receive an immediate response, and don’t send any further texts, or you’ll seem desperate. If he doesn’t respond, move on.

Chin Up, but Don’t Give Up

If it doesn’t work out, don’t fret. Most first dates are just that: a first date. Remember, it’s a numbers game. So look at these endeavors as recreation; eventually, first dates will be something you look forward to rather than dread. Get out there and make some new friends, get some nice meals, and have some fun!  

Read More:

Free Online Dating Sites for Women Over 50

Over 50 Dating: 3 Mistakes You May Be Making

How to Stay Safe Living Alone


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