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Dating Again - Advice for the Mature Man and the First Date

Updated on December 20, 2009

Fellow Hubber Jason Stanley left a great comment on my hub The First Date – Don’t Scare Him Off :

First date? Oh my God! I would be horrible on a first date, and probably if she sneezed, or said much more than hello I would break out in a cold sweat and bolt for the door. Clearly I have been married a looong time and the thought of going on a first dates is enough to bring me to my knees either from the shock or in prayer to end the pain.

Foolishness aside, since you did such a good job here, how about writing a hub on first dates for those who are "mature" (read older) and newly re-singled?

Thanks for the comment and idea, Jason, I appreciate it.

Dating is different when we’re older. We’re more set in our ways, a little less flexible. We’re also a little more insecure about our looks, or our age.

And don’t give me any shit for that, all you 45 year old knock-outs with all of your confidence and open minds. Surely you can figure out that many people don’t feel the way you do, even though they’d like to.

Here’s 3 tips for anyone breaking back into the dating world again at a more mature place in life.

1 - Don't scare them off.

In that Hub “The First Date, Don’t Scare Him Off” there is a basic theme you can take into your mature dating life. That theme is, don’t be scary.

Meeting your date for the first time is just like meeting anyone for the first time, from a new coworker to a new neighbor.

Relationships take time. This one is no different. Don’t start out with how your ex wife used to hate Chinese food, or how your ex wife got your condo so now you’re renting some crappy little apartment. It’s easy to draw similarities and comparisons, and to bring your ex up since this person was a huge part of your life for many years. This is going to take a conscious effort on your part. Resist the urge to talk about her. Be mindful of it. Don’t make it sound like you aren’t ready to move on because you’re still so engulfed in the past.

I’m not saying you can’t ever talk about your ex. If the first date turns into a second and third, believe me there will be a lot of conversations about your ex. But don’t start out with them. Just like meeting anyone for the first time, you don’t keep pulling out your baggage.

At your age, there should be MANY things about you that are fascinating that you can bring up and talk about on a first date. I’m sure you have a thousand memories that involve your ex. Do your best to leave the ex out of what you talk about. Focus on YOU. Focus on FUN.

Tell her you’re a Yankee fan. Talk about the season if she’s interested. Tell her you love Two and a Half Men, or whatever TV show or movies you like. Discuss them. Books you’ve read and liked. Tell her what you do for a living. Or about some great antique shop you found off Columbus Ave. Tell her about Young Frankenstein on Broadway. Items in the news, your dog, your expertise with MAC computers… There is so much about you that someone meeting you for the first time would love to hear.

And here’s another tip. Listen. Ask her about her job, her hobbies, her vacations, the movies she’s liked, the stores she shops in. Listen to what she has to say.

If she asks about your ex, you should be honest. Tell her. Answer the question. But try not to let the conversation get heavy. The first date is just not the time for that. Without sounding evasive, you might want to say something like, “Next time we get together, I will tell you more about this. I really have nothing to hide. It’s just that, I’m having such a nice time learning about you and looking forward, I really just don’t feel like talking about my ex right now if that’s ok with you.”

2 - Where you live matters

I wrote a HUB trying to point out the problems an immature bachelor pad will cause when dating. These ideas can be applied to a mature situation as well. While you probably don’t have the same exact issues, you still need to be mindful that your place can make or break a date.

Did your ex do the cleaning? Maybe that’s something you have to think about now. If you don’t have the time, hire a service. Did your ex do most of the decorating and shopping? Well, now it’s your turn. Some decent wine glasses, some new bedding, and a few candles never hurt anybody.

A mistake recently divorced guys tend to make in their new digs is the overabundance of nostalgia. I think this is especially true if there are kids involved. Maybe you think it makes the kids feel better about your place. Hey, I have no idea, not being a kid person myself. I’m not giving advice on how to make your kids comfortable. I’m giving advice on how to get laid.

But seriously I think this advice is good for your psyche too:

You’ve been a husband, partner, father… it’s time to be YOU. It’s time to stop defining yourself with other people. A man who knows who he is, is attractive.

You have a few pics out of your kids. That’s super. But that’s enough. It doesn’t have to be a memorial. And their Xbox doesn’t need to be in the middle of the living room. Your home shouldn’t show every woman that walks into your place for the very first time the massive amount of your life, time, and heart that she will never ever be able to compete with. Even if it’s true, remember that first date first impression thing. You can ease her into that as you both become more familiar.

No kids? Then this is easier. Remember that guy you were before you were married? That guy that liked the color blue but never had a blue room because the ex wife hated blue? The guy that liked Dali, or wanted a fishtank? Try to tap back into yourself. Don’t let your new place look like an empty little stop over. That’s just sad. Don’t be pathetic. Make it look like a home.

3 - So where do you find dates, anyway?

I wrote a HUB about online dating that you may want to check out. But for now I’m going to focus on your getting out and doing the live thing first.

Try bars. I wrote an article about that too, and I really hope you’ll check it out because I absolutely think it will help you get back out there.

Consider seeking out those places and events of special interest. Wine tastings, Jazz joints, sports bars – these are all great places with lots of opportunities.

But here’s a nice easy tip for starting out: The Happy Hour. Ask around at work. Odds are there’s a group there that hits one regularly. Even if it’s the girls that go, I’m sure they won’t mind your tagging along. Ask the guys in your gym if their offices go to any happy hours. Ask the guys you used to work with. Check out the happy hour info at places near you.

Chain places like Ruby Tuesdays, The Macaroni Grille, and The Olive Garden are good spots to try especially if you’re not in a major city.

The Happy Hour thing is designed for you. Professionals, on a schedule, trying to socialize, unwind and make new friends. It’s usually timed for right after work, figure 4 – 7pm. It won’t interrupt your schedule, and it won’t look desperate.

Network. Talk to anyone and everyone. You could make good business connections, meet a new work out buddy. If you do have smaller kids, you could even meet other weekend dads that might want to get together for a hockey game or monster truck rally or whatever it is you people with children do.

And last but not least, happy hours are a great place for single women to go to meet guys. It’s safe, it’s inexpensive, and it’s easy to work into your schedule. You’ve got a nice class of people at these things. And don’t forget, everyone you talk to at one of these is a potential networker. You never know who has a coworker, or a friend, or a sister, that might be perfect for you.

Jason, just be yourself. Be for real, try to be light and fun on the first date. Listen to her. Be a gentlemen. And keep looking forward.

Best to you.

Borat - Dating Service

If you liked this HUB please click the "Thumb's Up" below, just before the comments. Thanks!

All text original content by Veronica. All photos used with permission. All videos courtesy of


Submit a Comment
  • Veronica profile imageAUTHOR


    8 years ago from NY

    Thanks so much, John!

  • profile image


    8 years ago

    what a nice article and so well written!!!

  • Veronica profile imageAUTHOR


    11 years ago from NY

    thanks Mark!

  • Mark Knowles profile image

    Mark Knowles 

    11 years ago

    LOL _ I am still laughing from the Borat video. I have heard worse when I was single :) Nice hub.

  • Veronica profile imageAUTHOR


    11 years ago from NY

    Hey there G-Ma, hubber with a great name,

    Glad you liked the hub! And I'm glad you liked what I said on the forum about your name. Thanks so much for the fan mail, I left you some too. Feeling the love....


  • G-Ma Johnson profile image

    Merle Ann Johnson 

    11 years ago from NW in the land of the Free


    And I wanted to thank you also about the compliment you  gave me on the forum..

    This pic of me is truely me sweetie..You are a dear  G-Ma :o) hugs

  • profile image


    11 years ago

    This is great advice. You have a nice balance of opinion, observation, humor, and depth. I fall into this catagory of mature man dating again. This will be surely helpful.

  • profile image

    Alek Novi 

    11 years ago

    Nice. I love your writing style. Even though i've been writing on the subject for a while, I haven't gotten it this streamlined.

    I might steal a few "tricks" if you know what I mean.

    Excellent hub. Rated UP!

  • Wanderlust profile image


    11 years ago from New York City

    Great hub and absolutely true! Particularly this part "Don’t start out with how your ex wife used to hate Chinese food, or how your ex wife got your condo so now you’re renting some crappy little apartment." - that's actually a problem of many men and a major turn off for a woman.

  • Jason Stanley profile image

    Jason Stanley 

    11 years ago

    What a delight! A hub created on my question. Actually, I really am married - very happily for almost 25 years - and it was just the thought of every having a first date that scared the bejesus out of me.

    Your advise is timeless, fun to read, and really needs to be heard - I believe from both sides. I especially like the point that everyone that isn't a fit, may know someone who is.

  • Stacie Naczelnik profile image

    Stacie Naczelnik 

    11 years ago from Seattle

    This is fabulous. A divorced friend has problem dating - either the guys are too flaky, or they try to move too fast. She wants to take the relationship slow, especially as she has kids. The guy she is currently dating wants to move faster, and then she has to keep asking him to give her space (and if she has to keep asking, he probably will be asked to stop coming around completely). So, going slow is fabulous advice.

  • Veronica profile imageAUTHOR


    11 years ago from NY

    DedicatedMe, Thank you! Men need to hear this. Wouldn't a first date talking about music, art, you, sports, ANYTHING but his ex have been better?

    i may have to quote you on "the la la la la" I love that.

  • DedicatedMe profile image


    11 years ago from Florida

    You are so funny. I hope some single sap takes this article to heart. I've completely eschwed dating all together due to hearing about the ex, the kids, the la la la la la. All the ex thaerapeutic talk starts to sound like Charley Brown's school teacher after awhile, and as the squaking of the baggage continues, all you can think about is where to find the brightly red tinted light that is glowing EXIT! EXIT! EXXXXXXXXXXX-it! Kudos!


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