Dating After 50: Boundaries vs. Companionship?

On the subject of boundaries vs. companionship, I’ve been on the receiving end of two disappointing dating experiences lately. Perhaps some of you can relate to either one or both.

The Pitfalls of Dating

In the first, I was invited out to dinner. When he offered to pick me up, I said I would meet him at the restaurant. He asked again, and I gave the same answer. We agreed to talk before the date scheduled for two weeks later. I never heard from him again. In the second, I canceled plans with friends to make room for a Saturday night dinner. By the morning of the date, I hadn’t heard a word. When I called, he told me he was exhausted and would probably cancel. Later that day, he did.

Respect Boundaries

I could tell you why I think each of these men 50+ behaved this way, but I’ll never really know. What I do know is what I needed: a first date on my terms, and someone who showed up.

If you’re a Black woman over 50, you may be carrying stories like these, too. We’ve earned our independence, our peace, and our standards. A man who doesn’t respect a simple boundary like meeting in a public place isn’t someone we lost. He’s someone we learned about in time.

Here is how I’m handling it:

My 5 Dating Rules

1. Decide your rules before the invitation. Public place, your own transportation, a close friend who knows where you’re going and who you’re meeting. Deciding in advance means you’re never negotiating with yourself in the moment.

2. Watch how he handles “no” or “not yet.” A boundary is the cheapest, fastest character test there is.

3. Don’t empty your calendar for a maybe. Keep your plans with friends until the date is confirmed. Admittedly, this is tricky. We don’t accept a firm date invitation expecting it to fall apart.

4. Debrief, then reset. Call your girlfriends, laugh, and vent. Then close the chapter without writing a conclusion about all men.

5. Keep showing up. Accept the invitations but on your terms. Stay true to you.

Not Giving Up

I’m not done with dating, and I’m not bitter. I’m clearer. Two disappointments don’t make a pattern in the whole community, and they don’t change what I deserve.

Dating after 50 asks something of all of us. Being clear about both our boundaries and our expectations is at the top of the list.

So tell us: what is one boundary you will not trade for companionship? What are your expectations of a first date? Share it in the Mahogany Mates community. Let’s keep each other strong, discerning, and open.

Denise Kaigler is the co-founder of Mahogany Mates. She’s Black, single, 50+ and believes in the power of love. Even after disappointment, hurt and loss. You can reach her at connect@mahoganymates.com.