Ask Wendy

How Can I Tell When I’m Ready to Date Again?

Friday, September 14, 2018
12 Shares
middle aged woman holding tulips
Hey Wendy,

At 54, I’m in a financial pickle after a failed business endeavor. I own a house but have no savings and owe $15,000 in back taxes.

I’m bummed about my last failed relationships, am in therapy, but at least the breakup pain is no longer exquisite. Just low-grade sadness or bleakness. Relationships have always been my primary source of joy.

My house needs some decluttering and I’m in mid-repainting. I need to sell some items or give them away.

Then there’s the middle-age pudge that is too much to feel super sexy.

So, when do I start dating again and when do I know I’m ready? Should I spend another 6 months plodding along losing more weight, upping the income, improving the home feng shui? At 54, is there really hope for love again?

Stefani – Temecula, CA


Hey Stefani,

Great question!  Determining when you’re ready to date can be tricky. You’ve got to discern if you’re in good enough working order to be out there before you date. The good news is it doesn’t have to take you six months—in fact, it doesn’t have to take you six days if you’re motivated.

You, your living conditions, and your financial life do not need to be perfect, so let’s look at “good enough” one piece at a time. Ready?

Finances: No savings and some debt? Okay. Sounds like many people. Not ideal, but not abnormal. I hear you that your inner critic has plenty to say about where you should be financially at 54 (mine is talking my ear off about it, too), but you are where you are. So, your responsibility as a single person who dates is twofold:

  • Be able to pay for yourself on a date when you go out. It’s okay if your date treats you, but don’t rely on it.
  • Be transparent about your financial situation with anyone you’re dating seriously. This is not a first date conversation; this comes later (much later). And it’s perfectly acceptable to go out for coffee, or a drink, or a walk in a (well-lit, high-foot-traffic…what, I’m a city girl) park, or to do other free activities.

Your home: You are ready to date when you are ready to bring someone back to your home and be okay with what they find there. If your house is lived-in and slightly worn, that’s different than hoarder-level stacks of stuff. If you’re approaching the latter, however (and I say this with love), sort your shit out. Get a girlfriend to come over and help you over a weekend or two, because some of those things you think you need to sell might need to be given away or discarded, and thinking you will sell them will only keep them around longer and prevent you from moving on in your life. Is that a price you’re willing to pay? Our cell phones make it super easy to throw things up on EBay or Craigslist now, so make it happen!

Your body: This is the easy one. If you want to lose weight, cool. You can do that. But it’s not a necessary prerequisite for dating. Did you know there are guys who like women at your size? It’s true! There are men who love your body just as it is. And there are men who will love your face, and the body aspect is inconsequential. There are also men who will love your energy. There are men who don’t care about the actual shape of your body but how you move in it. See? No need to wait to date—you are datable and sexy at your size. “Fake it till you make it” is your best friend here. Work on exuding confidence in yourself, even if you don’t feel it yet. And once he’s looking at you like you’re the tastiest snack in the room, you just might believe what you see.

Your mental health: This is the toughest one, and I’m going to defer to your therapist on this one. Check with them and see if they think you’re in “good enough working order” to date. Then after they give you their opinion, check with your gut to see if that feels right to you, and make up your own mind from there.

I will say that most of us look for stability and joy in another person, and girlfriend to girlfriend, I think that this is a bit of a mistake. You might want to use some of this single time to learn to enjoy being a single person, as fleeting as this time may be, because do you know who makes the happiest partners? Happy people.

Is there still hope for love and relationships at 54? Absolutely! But only if you say so. Have you ever noticed that we humans are always telling ourselves stories, and then we buy into the narratives we spin regardless of whether they’re actually true? I know a lot of folks who say, “It’s too late for me.” Okay. If you say so. Or, “No one will want to date me at this size.” If you say so. Or, “that person could never love me, they’re too hot/successful/smart/funny/unobtainable.”

Mm hmm. If you say so.

There is not one thing wrong with being single, but if love and partnership are what you’re after, it’s available at 54, 64, 74, 84, 94 or 104. We’re the ones who put the brakes on what’s possible. Choose your story wisely.

Happy dating!

12 Shares
Do you have a dating, sex or relationship question for Wendy? Send it to 121datequestions@gmail.com.