7 Dating Challenges for Seniors

What dating challenges have you faced?

For many of us over 60, we’re at a point in our lives where we’re hoping to find serenity and harmony with someone special.

Maybe we’ve finally gotten out of a toxic marriage or long term relationship.
Maybe we were abruptly dumped by someone, but now coming to understand that it was for the best.
Or maybe we’re widowed – we lost the love of our lives – but are now willing to see if someone else special is out there.

So, here we are in the third act of our lives, ready to welcome someone new into our lives, but we may have to deal with some dating challenges . . . just because we’re over 60.

I advise that, before you get serious about anyone, know your deal-breakers and what kind of person your ideal partner will be. You do this as part of your dating game plan.

Don’t wait until you’ve fallen in love with, say, a smoker, to realize you could never be in a long term relationship with someone who smokes.

Click on any of the links below to go directly to that section:

3. Hands-on or live-in grandparenting/parenting

7. The older man/younger woman syndrome

1. Health Issues

We all know that things start giving out in older bodies. Sometimes it’s just those nagging aches and pains. Other times it’s more serious things, like heart attacks and strokes.

How many people over 60 do you know who are NOT on blood pressure medication? Fortunately, I’m not. But most of the men I dated were.

I also found that most of them were not taking good care of themselves. They were overweight, not exercising much, not eating healthy.

This certainly applies to lots of women over 60, too.

One of my dating deal-breakers revolved around health. I do take good care of myself. I don’t smoke or drink.

I (mostly) stayed clear of men who stated on their online profiles that they drank or smoked. And I knew I wouldn’t be happy with someone who ate a lot of junk food and fast food.

I remember one first-and-only date who told me he felt bad that he was so overweight, but said, “I’m trying to lose weight, but I can’t stop eating fast food.” He had given up even trying.

There were a number of reasons he wasn’t right for me. Just one of them was that I’d have a hard time living with someone who can’t stop eating unhealthy foods when it’s so important to me to take care of myself, with diet and exercise.

Chronic health issues like diabetes, cancer, COPD . . . the list is extensive . . . are dating challenges that need to be addressed. Some people put that information about themselves up front, on their dating profiles, so potential partners have a heads-up.

It’s important (and only fair) to share any health issues you have with potential long term partners early in the relationship.

Within the first few dates you probably have an idea of whether or not this might be “the one”, so be honest and give them the option to stay or go.

Your health issues may be more than they bargained for, or are capable of dealing with.

2. Addiction

America has a huge drug and alcohol problem:

“Deaths from opioids increased among Americans aged 65 and older by 53 percent in 2020 over the previous year, the National Center for Health Statistics found. Alcohol-related deaths, which had already been rising for a decade in this age group, rose by 18 percent.”

For sure, during the pandemic drinking alcohol to deal with any kind of stress or problems became more normalized. But the rise in substance abuse (and in particular, alcohol abuse in women) began well before that.

Chances are that sometime in your life, you’ve dealt with your own addiction or that of others you know.

Cosmo and I write frequently about addiction and dating in recovery, because we’re both in recovery.

We both knew it was a bad idea to even consider a relationship with an addict.

It is not possible to have a happy, healthy relationship with someone addicted to anything − alcohol, drugs, sex, gambling, etc.

Too much of their efforts and thoughts are focused on feeding their addiction. They don’t have room in their heads, or enough time in their days, to fully devote themselves to a relationship.

Cosmo wrote about the ways addiction sabotages relationships:

Secrecy and lies
Anger and/or abuse
Emotional damage to any children involved
Impact to finances
High risk of illness, death, or arrest

Many people finally get their acts together later in life and get sober, but for many others, the addiction lives on and has progressed to a dangerous level.

I wrote about the telltale signs that you’re dating an addict:

Making excuses for behaviors
Drinking or doing more drugs than intended
Their friends also have addiction issues
Appearing ill in the morning
Losing interest in hobbies

3. Hands-On or Live-In Grandparenting/Parenting

Many grandparents over 60 find themselves being the primary caregiver for their grandchildren. Their sons and daughters, for various reasons, are not there to raise their own children.

I came across quite a few men who had young children of their own that they were raising alone.

I knew myself well enough to understand that I wouldn’t be happy raising children at my age. I appreciated it when men in either of these situations plainly stated that on their online profiles.

Conversely, you may welcome having children in your day-to-day life at this age.

4. Retirement

You’re finally retired, or he’s finally retired, or you’re both finally retired. Yay!

But wait a minute, even that good news can come with some dating challenges.

We often hear about women going nuts because their retired husband or boyfriend is always around the house, idle and not knowing what to do with themselves.

Both of you being at home together too much can put a terrible strain on a relationship . . . especially a new relationship.

There are lifestyle considerations when one person is retired with plenty of leisure time while the other is still working.

If you are retired and have lots of leisure time, you may want a partner who’s in the same boat, and will spend lots of time with you.

It’s only fair to make that clear early on when you’re dating. Make sure your retirement plans are aligned with each other.

Remember that, even in the best of relationships, you each need time and space away from each other.

Try to strike a balance between the things you’ll do separately, and the things you’ll do together.

5. Money Problems

Money and finances can cause problems in any relationship, at any age.

In fact, they’re at the top of the list of issues that can tear people apart.

When you’re over 60, add into the mix that one or both of you may be on a decreased, fixed income.

With money tighter, money problems can escalate.

Before getting too deep into a relationship – and certainly before moving in together – have a serious talk about finances:

Do your best to determine each other’s spending habits.
Ask about any debt.
Be sure your partner has the wherewithal to equitably share in expenses.
If eating out and/or traveling frequently with your partner is important to you, be sure they want to do this, and will be able to afford it.

Discuss what kind of retirement each of you wants, and how you can help each other attain those retirement goals.

Read Cosmo’s article, Money and Dating Over 60 – How to Avoid Relationship Mistakes, to get advice on:

Who should pay for the first date
How you’ll know if you’re dating a romance scammer
When in the relationship to discuss finances
Figuring out money in a new relationship
Lying about money in a relationship
Financial things to discuss in a new relationship

6. Women’s Body Image Issues

It’s no wonder women have sometimes crippling body image issues. This is certainly one of the major dating challenges.

All our lives we’ve been bombarded with the ideal body we’re supposed to maintain all our lives – nearly rail-thin with smooth, supple skin and impossibly firm breasts.

We’re even somehow expected to have a “youthful glow” even into our 80s.

Women, too often, think of themselves as “old” at 60 . . . unattractive and not desirable to men.

Instead of being confident in and appreciating who we are, what we’ve done and how much we have to offer, we fuss, have “work” done and try desperately to hold on to a youthful appearance.

It can be so bad for some women that they avoid dating entirely so they never get to the point of shedding their clothing for intimacy.

My advice to women with this issue: Try not to let these thoughts keep you from dating and/or from enjoying dating.

Go out on lots of dates so you’ll gain experience.

I can almost guarantee that, over time, it will get easier. You’ll stress less and less about your body.

7. The Older Man/Younger Woman Syndrome

dating challenges, older man and younger woman

Although both men and women over 60 face dating challenges, women are sometimes hit with one in particular that doesn’t often apply to men.

As if it weren’t difficult enough for women over 60 to find eligible and worthy men, some men over 60 won’t even consider dating women their own age. They will only date women 20 or more years younger.

My advice to women: Don’t waste a minute fretting over this.

Those guys are not going to be right for you. They won’t keep you happy and they probably won’t ever be happy with you. They’ll probably lead you towards even deeper body image issues.

You have to figure there’s a level of immaturity in them that may always be there.

Although there may be plenty of men like this out there, I doubt that the majority of men over 60 fall into this category.

Most of them know enough to look at the whole woman, not just her outward appearance.

If they’re seriously looking for a life partner, they want someone who will be as compatible as possible . . . someone whose personality, sensibilities and lifestyle will fit with theirs.

On the flip side, there are lots of women over 60 who are only interested in younger men.

My feeling is that a relationship with more than a 10-15 year age difference – whether or not it’s the man who’s younger – may be on shaky ground.

But then again, since we’re all unique, there really is no ideal age difference that will seal the deal for a lasting relationship.

By the way, there’s a dating site that’s designed just for people who want to date people older or younger than they are, AgeMatch. It’s become popular with our readers.

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7 Dating Challenges for Seniors