Think You’re Ready to Date Again? Ask Yourself These 5 Questions First

Are You Ready to Date Again?

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Short and Sweet Summary: Deciding whether you’re ready to date again isn’t a decision most of us take lightly. It’s a pretty big step in our widow journey. But let’s not make it more than it is. Just ask yourself if you’re up for the possibility and see where it goes from there. That’s all.

How do you know if you’re ready to start dating again? What is the general consensus on how long a widow should wait before dating again? Do specific signs exist that show a widow is ready to date again?

Ahhh…all the questions! The answer is there’s no good answer. Deciding if you’re ready to date again is a personal decision and a huge hurdle in a widow’s life.

I mean, you’re agreeing to go out with a man who isn’t your husband. You’re probably thinking how messed up is that? But your husband died. You didn’t. You deserve to find some enjoyment in your life again because you woke up breathing today.

You’re still living, remember?

Why not ditch all the excuses as to why you shouldn’t be dating and ask yourself if you are ready to date. Not dating because you don’t think you should and not dating because you aren’t ready are two very different things.

Let’s take the “shouldn’t” excuse right out of the rotation.  It doesn’t belong here. There is no “should” or “shouldn’t” when it comes to widows and dating. The only thing that matters is if you want to and are willing to date again.

Don’t worry. If you’re not ready to date again, that’s OK too. You can still prepare for the possibility by asking yourself a couple of questions to make sure you get as much out of the dating experience as possible. You know…when you’re ready. Which might not be right now. No pressure.

Deciding to Date Again After Death
Image by Bitmoji

But if you are ready, let me be the first to say, YOU ARE AWESOME!

It doesn’t make any sense to me to be sad and lonely all the time. Absolutely no sense. So, good for you for realizing that you’re a living, breathing human whose needs include fun, companionship, and conversation. You deserve this. You do.

Now, before you go get all gussied up for an online profile photo, think long and hard about these 5 questions first. You need to come to grips with what’s really going on in your head before you set out to conquer the dating world. 


Waiting for grief to end is like waiting for Publisher’s Clearing House to show up at your doorstep. It ain’t never going to happen.

We know there’s no fix for grief.  We know we will mourn our husband’s death forever. So, if you’re waiting to date again because you think you need to stop mourning or stop grieving, you will wait (and remain alone) for a very, very long time.

It’s difficult deciding to date again.  I get it.  I made excuses, too. Pushed thoughts out of my head. Punished myself for thinking about enjoying life with someone other than my husband. I must surely be a horrible woman and widow if I even entertained the thought of spending time with another man.

Until I finally realized the negative self-talk and negative thoughts were just defense mechanisms designed to keep me safe. I won’t get hurt again if I don’t date. My heart won’t break again if I keep it cordoned off.  My kids won’t get close to anyone who could disappear at any moment. 

If you’re protecting your heart, I don’t blame you. It’s normal. Your defense mechanisms are on high alert. But grieving never ends. Mourning doesn’t stop. The only thing you accomplish by remaining alone is being lonely. Ok, so maybe you’ve convinced yourself you’re not lonely. Which is another defense mechanism? UGH. See the cycle?

Besides, everyone has different timelines and different grief methods. I won’t ever judge your decision to date or not to date. I’m just giving you permission 🙂

You are ALLOWED to want this. When you’re ready. No pressure.


The single biggest hurdle to get over is believing you are worthy. I know you’re worthy, but it doesn’t matter what I believe.

You must believe in the far recesses of your soul that you are beautiful, amazing, witty, fun and totally dateable. No hijacking thoughts like:

  • I’m too fat
  • I’m too old
  • My right leg is shorter than my left leg
  • I have too much emotional baggage
  • My stretch marks look like the London tube map
  • I have overactive sweat glands

Do you see where I’m going with this? We all have reasons to doubt our innate worthiness. But everyone is fighting battles we know nothing about. If the pit stains on your shirt embarrass you to no end, just remember some guy’s eye twitch kicks into high gear when he’s nervous. For every stretch mark you have, some poor soul lost another strand of hair on his way to baldville.

Do You Believe You're Worthy?

It’s always something.

If you don’t think you’re worthy you won’t attract worthy suitors. Period. Until you can look at yourself in the mirror and say, “girl, you’ve got it goin’ on!” you won’t be in any position to start that online profile.

Regardless of your baggage, broken heart or bifocals, someone else out there deserves to know how amazing you are.

Only if you believe it first.


Grieving a death isn’t for the faint of heart. It takes some serious stones just to get through most days let alone think about a potential future. A future that might include another human being of the male persuasion who isn’t your husband. Can’t we just go back to the way things were, when everything was normal and grief wasn’t seeping out of our pores?

No, unfortunately, we can’t.

The past is part of our lives, but we don’t need to live there. I’m not suggesting you forget about your past. That’s impossible. I’m asking you to let go of the stranglehold it has on your life. Life was certain when your husband was alive and you were comfortable in your certainty. Now it’s not. It’s completely uncertain. That’s terrifying.

But you have the option to start a new chapter in your life. Even though uncertainty can be terrifying, it can also be liberating. You get to write the new chapter. Say and do whatever you want. If your new chapter includes dating, you can set the parameters however you see fit.

The past brought you to where you are today. However, you get to decide which direction you’re headed in tomorrow.


Whoa there, Nellie!

Don’t get too far ahead of yourself just yet. Another sneaky defense mechanism we use to justify why we have no problem ending up like an old lady with 16 cats and gnome figurines in our front yard is that we don’t think we’ll ever get married again.

Old Lady with 16 Cats
Photo by Paul on Unsplash

Who said anything about marriage?

Good lord, people. We’re talking dating here, not merging families like the obviously (totally) fictitious Brady Bunch.

Dating means meeting someone for coffee. Going out to lunch after church. Having a partner for a Friday night Euchre card party (shout out to my Midwest peeps). It doesn’t have to mean anything else. The point is, you’re getting out of your house, wearing something other than yoga pants, and applying lip gloss so you don’t look like the living dead.

Dating doesn’t have to mean anything other than going out socially with another human being. If you put too much emphasis on anything other than that you are missing the entire point of meeting other people.

Good luck with your cats.


Opinions are like assholes. Everybody has one. If you put too much emphasis on what other people think you may never date again. No one, and I mean no one, not even other widows, has any idea what your grief timeline means to you. You get to decide what’s best for you at whatever time you deem sufficient.

People can say, “oh, I could never date so soon after the death of my husband.” Or they could say, “Two years is long enough, you should start dating again.” Hmmnn…unless someone has walked in your shoes they really have no place to say what they think you should or shouldn’t do.

But, if you’re ready, willing and able to start dating again you need to make sure you don’t worry too much about what other people think. Someone will think it’s a good idea. Someone else might think it’s a bad idea. Who gives a royal rat’s ass what other people think? This isn’t about them. It’s about you and deciding what’s best for you. Not what’s best for you mom or your hairdresser or your pastor or the massage therapist you spill your guts to bimonthly.

Therefore, your opinion is the only one that matters.


Deciding whether to date again isn’t a decision most of us take lightly. Ultimately, it’s a pretty big step in our widow journey. But just because it’s a big step doesn’t mean we need to make it more than it is.

For example, dating is just going out socially with someone else. That’s all. Before putting undue pressure on yourself to figure it all out before that first coffee date, relax. You don’t need all the answers right now.

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