My partner (and true love) Daisy reveals several great smart dating tips for women over 60 in this article. Since men sometimes (all the time?) do things a little differently than women, I’m going to cover some of the same dating advice here but from a man’s perspective.
If you’re a man over 60, it’s quite possible you’re re-entering the dating scene after a death or divorce. Perhaps it’s been many decades since you’ve been on a date. Technology has evolved at warp speed. Online dating might feel like an impenetrable, puzzling world better left for millennials. And where do you start these days with offline dating?
Never fear. You can take comfort in the fact that human psychology never changes. When you come to understand your potential dates’ psyches and your own needs and wants, you rise above your ‘competition’.
Smart Dating Tips for Men Over 60
Technology is the easy part of the dating scene. Technology, whatever its form, is simply another tool to use in your dating search. The hard part is, and always has been, learning how to successfully navigate the human-to-human connection. And since you probably are over 50 or 60, you’ve got a leg up on the rest of the world because of a lifetime of experience with your fellow humans.
So let’s talk about how to find and connect with the mature woman who could be your true love.
Follow the Directions for Successful Mature Dating
Daisy talks about the similarity between job search (her professional field of expertise) and dating. It works, because she used her proven job-search tactics to find her ideal partner—twice.
My professional background is in sales and marketing. Job search. Sales and marketing. When applied to dating, techniques and strategies from both of these fields work because they rely on understanding human psychology and human emotion.
We’re packaging and presenting ourselves to attract a woman. We just want to refine our “packaging” so it authentically displays who we are and attracts a woman who is right for us.
So how do we close the sale, or land that job, so to speak? Most men I know, myself included, rarely open the directions. Or they’ll read them only when they hit a snag. So, too, you probably want to jump right into dating.
Don’t do it. I’m suggesting you pause and follow directions proven to work in our Mature Dating Game Plan. As a mature man, you’ve probably learned that it often pays to listen to the voice of experience. Here are two things that will help you.
First, accept that the mature dating process is going to take a while.
You might get lucky early on as I did. But typically, as in sales and marketing, you often go through many prospects to get to your first customer. In a job search, you do many interviews before you land the right job.
When I started dating again, I told myself I’d be fine if I never found anyone. My life alone was very good, and I figured I’d just enjoy the experience of meeting a lot of new, interesting women. I was perfectly OK with that scenario. Ironically, I met Daisy almost immediately.
So, I urge you to maintain an “acceptance” frame of mind. It removes the self-imposed pressure of dating and makes it more relaxed, fun, and easy.
Second, you need to do a little preparation, similar to what we’d do in job search or marketing.
It’s not hard at all. It just takes some time, but it pays huge dividends.
You want to make sure you know yourself, just as if you’d know your product or service inside and out before you ever presented it to a customer.
Then you need to know who your ideal partner will be. If not, how will you ever find them? In marketing the first task is always to create a detailed customer profile. That way we know where to find them and how to talk to them. And most importantly, we’ll recognize a good prospective customer (our ideal partner) when we see one.
You can probably do your prep in one afternoon. Once you’ve done this, you’re ready to think about dating.
Setting Up Your First Date
Here are some things to keep in mind when you’re setting up your first date.
Of course this varies according to where you meet your potential date. If you meet a woman at work or an event, it’s handled a bit differently than an online meeting.
If you meet online, you’ll want to email a few times to get to know her, over the course of a week or two. If it feels right and she fits your ideal partner profile, then set up a brief phone call.
By getting to know her in this fashion, you can find out if she’s suitable. It’s much easier to do this in a relaxed manner, via phone and email, than trying to do it on a stress-filled first date. If you see any red flags that you shouldn’t be dating her, then don’t. No need to waste her time or yours.
On the plus side, this additional communication will give you some things to talk about and help you get to know one another. This removes much of the stress and adds to the pleasure of meeting your new date.
If she seems to be a good fit, then set up the first date. Meeting for casual coffee during the day is best. A casual, relaxed event like a street fair also works as long as there is an easy out for both of you. That way, if the date is great, you can stay as long as you want. My first coffee date with Daisy went so well it lasted about four hours.
Whatever you do, avoid a full meal on the first date. And don’t insist that your date go to dinner. You don’t have to impress her in that fashion. This way if your date is awful, you’re not stuck waiting for a lengthy meal to end.
Let her pick the place with which she’s comfortable, preferably a place you both know, but strongly encourage a coffee date. Do NOT try to pick her up at her house. Meet at the agreed upon location.
It’s up to you to do as much as possible to make her feel comfortable and secure about meeting you.
Preparing for the Actual Date
What to Wear on Your First Date
You never get a second chance to make a first impression, so dress up a little. Don’t wear your stained deer-hunting jacket or the sweatpants you wear around the house.
For us men, it’s actually very easy to dress well for your first date without doing much. On my first date with Daisy I wore blue jeans with a traditional blue blazer, a plain white cotton dress shirt, and casual shoes that were cleaned and polished. Nothing fancy but still a bit dressy. Daisy noticed and remembered exactly what I wore, too. So pay attention to your attire, gentlemen.
You could simply wear a nice sweater to dress up almost anything you wear. Another alternative is to wear a clean, pressed, dress shirt or polo shirt without a jacket or sweater. A tiny bit of effort put into your appearance goes a long way to making yourself attractive to your prospective partner. In addition, it makes you feel better, more confident, and more at ease.
Incredibly, there are people who ignore this when they’re meeting someone new. I like to believe, perhaps naively, that most of us naturally want to smell good, feel clean, and look presentable.
Although it seems too obvious to have to state, be sure to brush your teeth and shower beforehand. Remember too that the stress of dating might cause your mouth to dry out and get a little funky. Keep mints on hand and pop one before you meet her.
Prepare Things to Discuss
Be ready to answer the typical questions such as, “Tell me about yourself” and “What are your hobbies?” Think about what you want to convey about yourself.
Make sure your online dating profile is accurate because she will be reading it. Don’t use that photo from 30 years ago. You can only find your ideal partner if you are honest about who you are. When you misrepresent yourself, you might get more dates, but you’ll never establish a trusting, honest relationship.
In turn, review her online dating profile and social media accounts. Google her name if you have it. Bear in mind that you might not get her full name until a later date. I offered up my full name during our initial email correspondence to make my prospective dates feel more comfortable. Women will naturally be less inclined to offer up their full name, for safety reasons, until they get to know you. So don’t press them for it.
If it’s a blind date or she was referred by a friend, ask the friend to give you a few details about her life. With the info available, you’ll have plenty of things to discuss.
You can write all these details down but leave the list in your pocket when you’re sitting across from her. Daisy said she had one first date during which the guy pulled out his list and started running through them like an interview. Don’t do that. She won’t feel good being grilled by you. Just commit a few things to memory and let the conversation flow naturally. If you need to refer to your list, excuse yourself and do it in the men’s room.
Tips for Navigating Your First Date Successfully
Relax. If you meditate, this is a good time to make sure you do it daily. It puts things in perspective. Remember it’s only one date. Keep your perspective.
Smile when you meet her. Smiles are proven to calm your nerves, to make you look better and more confident, and to give her a good first impression about you. Smiles are contagious.
Break the ice with something that will put you both at ease. Don’t do something outside your personality either. If you’re lousy at telling jokes, don’t tell a joke to break the ice. It won’t work.
Keep things positive and upbeat. Don’t talk about your exes or gripe about people, your job, or anything else. Avoid talking about sensitive subjects on your first date, like the ones below:
- Past relationship or marriage
- Family problems
- People not known to both of you
- Politics and religion
While these are all important topics to consider for a potential relationship, they’re best saved for a later date.
Be a Good Listener
A friend once told me there’s a reason we have two ears and one mouth—we’re supposed to listen twice as much as we talk. If you’re a talker, make an effort to actively listen more than normal. You’ll almost certainly hear things to talk about, which in turn makes for a more natural, flowing conversation.
I once had a dinner date in which the woman talked for hours without stopping. It wasn’t a pleasant experience and I truly don’t remember anything she talked about. It’s also more confirmation that a “coffee date” is best for first dates. I was trapped far longer than I needed to be!
And guys, please don’t be gross. An article on huffingtonpost.com, 8 Dating Turnoffs Men Over 50 Should Stop Doing, talks about a fellow who started a date by sharing that his dog had a bad case of fleas…after he hugged the woman. You can imagine how gross she felt from that moment on.
Offer to Pay for the Date
My feeling is that men should always offer to pay, especially if you initiated the date. Even if the woman invited you, make the offer anyway. You might end up splitting the bill but the offer itself presents you in a good light.
Should you kiss her when she leaves? Kissing is very intimate. The most you should do is a light kiss on the cheek when saying goodbye, perhaps combined with a hug. Avoid kissing on the lips, even if you feel the chemistry. If there’s a spark there, it will keep flickering until later dates. You don’t want to risk turning her off before you even get to know each other.
As my grandmother used to say, don’t forget your manners. For instance, take her coat for her when she arrives and help her put it on when you leave. Pull her chair out for her. Let her order first. Escort her to her car. I forgot to walk Daisy to her car on the first date and she noticed. It certainly wasn’t a deal-breaker, but all these little things are noticed by women and they add up—hopefully to the plus side if you’re paying attention.
But give yourself a break, too. We’re only human and when stressed, even good stress like a first date, we can make mistakes and forget to do things we normally do.
What if you have an awful first-date experience?
Don’t worry about it. It’s part of the process and you have other dates to prepare for. If you happen to like her but she obviously doesn’t feel the same, let it go. You can’t force it.
How to Follow Up After the First Date
As we re-enter the mature dating scene, we want to remain proactive throughout the entire process. Always follow up. Don’t just wait to see what happens.
Say “Thank You”
Send a quick text (if you feel texting is okay) or email thanking her for a nice time, even if you don’t want a second date.
Is She a Match for You?
Make notes on what you like and don’t like about her. If these items are not on your ideal partner profile, (that’s the homework you did in advance, using our Mature Dating Game Plan) add them to your list.
If you don’t want a second date, also say something innocuous like “I don’t think we’re right for each other. I hope you find the right one for you soon.” There’s no need to go into a detailed explanation about either one of you.
If you DO want a second date, also say something like “I’d like to see you again, if you’re interested.” If you don’t get a response after a few tries, then let it go.
Going Beyond the First Date
If you connect with one of your first dates and decide to go on a second, that’s awesome. It’s what you want.
However, don’t jump too quickly into a commitment, especially if you just returned to the dating scene. Continue to date others and be sure to be open about it with the women you date.
At some point you’ll meet the “right one” and make a commitment to a relationship. You’ll know you’re on the path to finding your true love if these things begin to happen.
In the meantime, you need to get to know your potential partners better as you get to the second and third dates and beyond.
As you get to these later dates (but still early in the game), that’s when it’s time to talk about all those important issues we avoided on the first date – health problems, addiction (past or present), family commitments, and lifestyle preferences.
If there are any deal-breakers, they’ll probably come up in these conversations. So don’t wait for too many dates to discuss these topics—just don’t do it on the first date.
What about sex and the mature dater?
I’m a believer in monogamous commitment first. When sex enters the picture too soon, it can stir up emotional chaos if there isn’t a secure, committed foundation for the relationship. It blurs boundaries and clouds judgement. It can lead to hard feelings and a sense of emptiness.
Of course, this is very much an individual preference, but whatever your philosophy, you should be in agreement and discuss it before you have sex.
Daisy and I mutually agreed to wait a few months in order to get to know each other fully. It gave us time to fall in love. This made it possible for sex to be but one expression of that love.
Zen Master, Thich Nhat Hanh says in How to Love:
“Sometimes we think that if we have sexual relations with someone, we’ll feel less alone. But the truth is that sexual relations don’t relieve loneliness.
There’s a Vietnamese poem in which the young man has the impression that he must sit very close to his beloved to relieve his loneliness. We have the impression that if we sit close to each other we’ll feel less alone.
If we’re separated by five meters, that’s too far. Four meters is better. Three meters is still better. But even one millimeter is still too far.
When our bodies are very close, we feel it will relieve this loneliness. But if we don’t share our aspirations and what’s in our hearts, then even if we live together or have children together, we can still feel very alone.”
If you’re honestly searching for your true love, you can wait for love to bloom first. The payoff is so much greater than any instant gratification you might get from having sex too soon in the relationship.
If you have a tip that’s helped you on your first dates, please share with us below!
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