Do we truly need rules for dating women over 60? It depends. Hopefully, a mature single person will draw on their lifetime of experience to handle their dates with wisdom and compassion.
But as the old truism goes, much of our experience comes from bad judgment and we’re all subject to one more bad decision or faulty judgment.
Also, the fact is that being thrust into the dating scene after decades away from it can be an alien experience.
If we’re in our fifties and beyond, our last dating experience might have been as an immature twenty-something. If we sub-consciously revert to that youthful dating behavior, it might not be the best thing to draw upon as a resource!
Yet with maturity I’ve learned the best guidance for a return to dating can come from within. All those years of experience can be distilled into an actionable plan for dating success in your search for true love.
9 Tips for Dating With Mature Women Successfully
Here are nine rules of dating for men that will make your mature dating experience a good one.
1. Know yourself before you start dating.
Do you know what you really want from your dating?
It’s almost a sure bet that it’s not the same thing you wanted when you were twenty. Yet your mind might automatically revert to the 20-year-old dating mentality.
Several years ago I was walking through Key West one evening. I started to comment on how nice it was that there were so many fathers and daughters strolling together.
They were gray-haired 60-somethings strolling along with their 20-something dates. Although they were in their sixties, they were thinking with their 20-year-old brain.
Take time to get to know yourself better before you let your long-buried wants and beliefs take over. I’m fairly certain that there weren’t many deep conversations going on between those old-young couples.
If you are newly divorced, widowed, or new in recovery, give yourself at least a year to process the changes going on in your life. Major changes take time to get through. You don’t want to attempt a new relationship while you’re still healing. It’s not fair to you or your partner.
2. Know what you want in your partner.
When you know what you want in a partner, your search for a partner is so much easier.
For instance, let’s say you’re a kind, considerate, gentle person and you want the same in a partner. Your date looks great and sounds fantastic on the phone. You meet for coffee and she instantly starts bad-mouthing a waiter. You can eliminate her as a candidate because she’s inconsiderate. Without your list of what you want, you might be tempted to continue based on looks alone.
By writing your list in advance and getting a clear mental picture, you won’t overlook any “no-go” qualities.
However, if you’ve had a series of failed marriages or relationships, your people picker might be broken. Although you think you know what you want, and maybe even list them specifically, there are subconscious motivations that can cause you to be attracted to, and to attract, the wrong kind of partner.
If so, take a time-out for therapy before you head back to dating. It’s an investment in time and money that pays off in happiness and joy.
3. Be honest and caring.
There’s no time to waste with immature games. We should have grown beyond that.
Don’t misrepresent yourself. I’ve seen many people who try to be who they think their date wants them to be. It never works. If you don’t like yourself, change those things that can be changed.
Be honest in your communication. If you say you’re going to call your date, call her. If you’re not interested, be kind enough to end it right there without leading her on. You can nicely thank her for a good time and let her know you don’t plan to continue.
Two examples from 10 Ways to Turn Down a Second Date at The Good Men Project are a good example of how to do this:
“You’re awesome and deserve someone great, I just don’t think I’m that guy.”
“I don’t see this going in the direction of a serious relationship and that’s what I’m looking for.”
4. Let the past remain in the past.
As is often heard in Alcoholics Anonymous, “we will not regret the past nor wish to shut the door on it.”
The past with all its pain and glory is a stepping stone to today. Hopefully you’ve learned the lessons you needed to learn and have grown as a result.
The last thing you want to do is create a relationship based on shared horror stories.
Yes, you’ll discuss those later in the relationship. But you don’t want your baggage to be the foundation, the common ground for your new relationship.
5. Don’t settle.
Settling is never a good idea for anyone in search of their ideal relationship partner. If you know who you want in your partner, and you present yourself honestly to the dating world, have patience. You’ll find each other.
In addition, statistics favor men with respect to dating…sort of. According to the US Census Bureau statistics on marital status and age, men continue to die at a younger average age than women. That’s the bad news. The good news is it means we have a much larger pool of potential partners from which to choose.
As of 2016, for every 100 single men over 55, there are 183 single women over 55. And the spread increases with age as you can see in the chart below.
6. Dress the part.
Hopefully you take good care of yourself physically as well as emotionally. When you go on a first date, it’s your only chance to make a good first impression. Do it.
As I mention in this related article about first-date anxiety,
“…those first impressions and judgements can overrule everything else people might later learn about you. Studies prove this repeatedly, and smart women daters will be looking very closely at what you wear.”
Of course, as we already mentioned you don’t want to mislead your date. Dress in a way that’s congruent with who you truly are. (See, you really have to know yourself well.)
7. Let her set the pace.
First dates are stressful for both men and women, but women have the added worry of safety. You can set a relaxed, safe tone by letting her set the pace.
Your first date should be a casual get-acquainted coffee somewhere informal that you both know, but give her the option to select. She’ll want someplace comfortable and safe. Don’t insist on a dinner date. Don’t insist on driving or on picking her up.
8. Set guidelines for when you’ll have sex.
Let the emotional attachment happen first before you make love the first time. Of course, most of what we write about here is about how to date with the intention of forming a true, loving partnership.
If that’s not your intention—if you just want hookups—then be clear about that with your potential partners. But usually that kind of shallow connection neither endures nor satisfies.
9. Be prepared for easy, fun conversation.
You’re just getting to know her on the first dates. Avoid first-date conversation-killers such as sex talk, swearing, politics, religion, or exes. You’ll get to those later.
For now, memorize a few conversation starters. Remember to listen twice as much as you talk and stick to harmless topics. Don’t forget to smile!
Final Thoughts on Dating with Mature Women
As with everything in life, there should be joy in your dating. These “rules” for dating after 50 or 60 are guideposts based on our dating experience. We hope they help you find that joy in what can admittedly be a scary experience, even for us men!
- Know yourself.
- Know what you want in your ideal partner.
- Be honest and caring.
- Don’t bring out the baggage.
- Don’t settle.
- Dress the part.
- Let her set the pace.
- Let the emotional attachment happen before you have sex.
- Be prepared for easy conversation.
Please feel free to share your senior dating stories and comments below!
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