Dating Again After 60: Ready or Not?

My own story of dating after 60 may be similar to yours.

When I decided to take the plunge, it felt like a monumental leap. I hadn’t been on a first date since I was 20, when I met my future husband.

I got divorced 30 years later and was then single for about 7 years. At some point, I realized that if I didn’t want to grow old alone and live alone, I had to be proactive about finding someone.

Asking everyone I knew if they knew someone didn’t pan out, I don’t drink so bars were out, and other traditional dating was a bust.

So I turned, hesitantly at first, to online dating and everything fell into place. But first, I got myself ready to date.

I’ve written before about the steps I took in my article, How To Find Your Ideal Partner.

I truly believe that spending that time preparing to date was what helped me find true love twice dating again after 60.

Dating Again After 60: Ready or Not?

Below you’ll find some articles Cosmo and I wrote about how to know if you’re ready for various aspects of dating, often based on our own experiences.

Am I Ready for a Relationship? [Quiz], by Cosmo

We know that many of our Smart Dating Over 60 readers here, mostly middle age and up, are returning to dating because they want a serious, committed relationship.

This return to dating might have been triggered by any number of life events:

They lost a spouse to illness or accident
They divorced
They’ve been single for some time but now that they’re retired, they have time to search for a partner

So, it may have been decades since they last dated. Naturally, the very act of dating is probably going to feel uncomfortable.

Another factor is the lifetime of habits, routines and behaviors that have set in. Will they be able to mold themselves to a new partner’s lifestyle when it turns serious?

These are all good reasons why a re-entry to dating is the perfect time to check relationship skills.

Take our “relationship-ready” quiz.

Single Women Over 60: Dating Again After a Bad Break-up, by Daisy

I was in a bad marriage for 30 years. After my divorce, I took a few years to get my head on straight, before diving into dating.

Even so, when I first started dating in my late 50’s, I was attracted to men who weren’t right for me, and perhaps weren’t right for any woman.

I was one of those women who fell for “bad boys” who were emotionally distant. They shielded themselves with sarcasm, and weren’t capable of having a mature relationship.

It dawned on me pretty quickly that I needed to look inward and figure out why I hadn’t had successful relationships. Why I kept picking men with whom a healthy, happy relationship was doomed.

Among other things, I thought long and hard about what things were important to me and what things would be deal breakers.

How to Tell When You’re Ready for Online Dating and True Love, by Cosmo

When my last relationship ended, I gave up on ever finding true love.

Relationships seemed to be out of the question for me so why bother to date? I believed there was an emotional demon lurking deep inside that simply couldn’t be exorcised.

Telling myself that it was my duty to abstain from future relationships, I was convinced it was the only way to avoid doing emotional harm to another.

That decision offered a sense of relief, calm, and acceptance. No more would I be plagued by an inability to successfully navigate a relationship.

And since there were to be no relationships, there wouldn’t be any dating. Yes, I was ready to give up on true love, companionship, sex, and true partnership.

Nevertheless, I wanted to figure out why my romantic relationships, despite good beginnings, always came to an end.

Finding Yourself and Starting to Date After a Long Marriage or Relationship, by Daisy

As noted above, I was in my late 50’s when I started dating again after my divorce.

The last time I had dated was in my 20s.

The kind of person I wanted in my 60s was nothing like who I wanted (or thought I wanted) back then.

Back then I had picked the wrong kind of person for me and I foolishly married him.

But more importantly, back then, I didn’t go into dating with an understanding of who I was and what I wanted from dating.

Whether you’re starting to date after an amicable or bad break-up, or the death of your partner, it makes sense to put thought into what dating will mean for you.

After all, you may not have dated for years or even decades.

What does dating look like now?

And what do you want from it?

Mature Dating: 5 Reasons You’re NOT Ready for True Love, by Daisy

The desire to have romance and true love in your life when you’re over 60 may compel you to leap into dating when you’re really not ready.

You may have lost a loved one in the recent past.

You may still be suffering from the break-up of a serious relationship.

Or, you may not have done any of the critical initial introspective work . . . without which you’re likely doomed to move from one failed relationship to another.

Whatever the situation you’re in now that finds you single, if your goal is finding true and abiding love, I urge you to think twice before you leap into another relationship, or even consider seriously dating.

First, take the time to look closely at yourself and fix anything that may hold you back, such as:

Addiction and/or substance abuse issues
Not being honest about who you really are
Not considering who your ideal partner in true love is
Being willing to settle, just to have someone in your life
Not being truly willing (or able) to let love in

Finding Love After Widowhood: Are You Really Ready To Date Again?, by Daisy

Is finding love after widowhood a challenge for you as you’re dating (or thinking about dating) later in life?

When you’ve lost a loved one, the pain and loneliness may be so great that you dive too quickly into a new relationship.

When you’re over 60, your children are probably out of the house. You may suddenly be all alone, rattling around an empty house and feeling acutely lonely.

Having a new partner, someone special in your life again, a soulmate, is a comfort . . . even just being physically close in a non-sexual way to another human being.

Without even realizing it, you may be driven by an overwhelming need to quickly replace the loved one you lost with someone new.

But diving into a new relationship right away may hinder with the grieving process.

Sex and Dating After 60: When to Have Sex For the First Time, by Daisy

Has this sex and dating scenario happened to you?

You’re on a date and everything’s clicking.

It’s early in the relationship . . . maybe it’s the first date, or you’ve only had a few dates.

You really like him or her, and you’re clearly extremely attracted to each other.

You can’t control yourselves and things kick into high gear from one moment to the next.

Suddenly you’re on your way to the bedroom and clothes are flying off.

This may be the beginning of a beautiful relationship. Everything may work out, and your relationship may thrive and grow in a healthy way. It may develop into true love. You may have found your soulmate.

But more than likely, the relationship is doomed to crash and burn . . . probably pretty fast.

Having sex too early can kill a relationship before it’s had a chance to catch hold.

Senior Dating: Are You Ready To Move In Together?, by Daisy

So you’ve been dating someone special for a while. Things are going well. You’re thinking you should move in together. But is it time?

How long and how often have you seen each other?
How well do you know her or him?
What DON’T you know about her or him?
How well is the relationship going?
Will moving in together ruin the good thing you have?

Along with marriage (which may well factor into everything, if that’s what you both decide to do), the decision to move in together should not be made lightly.

Moving in together is a big decision to come to.

If things go bad, it can be difficult to extricate yourselves, once you’re living together.

And the fact of living together may cause the relationship to fail, if you haven’t considered all the angles that come with it.

Taking this step means you’re ready for a deeper commitment to each other.