Dating: when will I be ready?

I’ve been a widow for 3 years now. All you have to do is read any post on this site to know that this journey is one filled with sadness, pain, suffering, confusion, anger, and hope. You’ll find women with ranges in their healing while we all navigate such similar challenges along the way. In this phase of my own journey, I’m wrestling with the idea of dating again.

I don’t want to be on my own for the rest of my life but I also don’t want to seek out the same relationship I had with my husband. I’m in a different phase in my life and I know that I’m looking for something different. Different how?? I don’t exactly know yet. Which leaves me wondering if I’m ready to get out there if I don’t really know what I want. And the kicker question, when will I know if I’m ready?

I don’t even know how I’m supposed to know when I’m ready. It’s not like studying for an exam where I put in time and energy and then test day shows up and know if I’m ready or not. Dating seems like such an unknown to me.

Do I declare widowhood in my profile?

How do I not fall into the comparison game?

Will I be able to kiss another man?

Will I have a total meltdown being intimate with a new person?

What if I don’t have a meltdown….what does that mean?

And if sex is horrible and it makes me miss my husband more?

Will it feel like cheating?

The list of questions can go on and on in my head to the point that I’m left spinning in my own sea of confusion that doesn’t have any answers. Which then takes me right back to the beginning, when will I know when I’m ready?

It’s possible that I’m never going to be 100% ready to start dating. Maybe, I need to adjust my expectations and take the leap when I’m 60% ready. The truth is that I’m a risk taker in many ways and I don’t wait until I’m 100% ready – I usually wait until I’m a good 60-70% ready before I leap. If you asked my family and friends, they would tell you that I’m a leaper and take risks in my business and in finances. Leaves me wondering what it would be like to apply this approach to my dating life (that’s currently non-existent)?

I can tell you what would happen – I would jump on a dating app and not have too many expectations. I would find fun in the process and not be focused on the outcome. Adjusting my goals and visions as things move along and negotiate changes as needed. I would ask for help when needed. Taking measurable and informed risks to move towards my goal. I know that this is what would happen because it’s how I approach all of my other life goals. I leap.

So many women on this platform have taken so many leaps. Getting out of bed each day and engaging in life is a leap each day. I’ve found joy, connection, bravery and boldness on this path so far and as I write this, I can see that dating would be the next step in my bold journey. Life is so messy and I’ve let go of wishing for it to be easier. I think that dating is truly allowing oneself to love and make space for another. I know that I’m capable of this and I can survive heartbreak if that’s what is at risk.

Who would have thought that dating was such a risk-taking step? Cheers to taking some risks in life and gambling on myself