Just the Tip is a sex and relationship column hosted by queer non-monogamous kinkster Jera Brown. Here you will find interviews with sexuality researchers and educators as well as smart and compassionate responses to anonymous questions. If you would like to be interviewed or have a sex or love question you’d like Jera to answer, email justthequestions@gmail.com or DM Jera on Instagram or Twitter @thejerabrown.

How can/should I comfortably get back into dating with a quality guy as a divorced 50-year-old woman who has had a bilateral mastectomy without it feeling like such a hassle?

I seem to attract men that think I’m lonely, and want a sexual relationship only.

They don’t seem to mind my “titlessness.” I tell them right away, almost hoping they do mind and will leave me alone.

I also have two daughters aged 21 and 15. My 21-year-old has a daughter aged a year and a half. The thought of dating men that could be perverts, or have friends that are seems like something I can control by not dating.

Is It Possible to Date Without It Feeling Like a Hassle?

According to Merriam-Webster, a hassle is an annoying or troublesome concern. It’s an inconvenience.

Whether dating feels like a hassle depends on your perspective going into it. But, no matter what, it’s going to take time and energy.

The things you work the hardest at are usually the things with the biggest payoff. And dating is no exception.

Some of what goes into it:

  • Work figuring out what you actually want, assessing your priorities and how you want to present yourself.
  • Work deciding what your boundaries are and sometimes work maintaining them.
  • Work vetting people, and preparing to be rejected or do the rejecting.
  • Work processing emotions — good and bad — that come with new experiences.

Deciding to open yourself up to new love or even sex is like deciding to travel to a new country. Yes, you’ll “come home” with stories. You’ll discover things about the world and about yourself. But it takes energy. Especially to do it in a healthy way. 

There’s one caveat here. Putting work into an unhealthy or failing relationship doesn’t always equal a happy ending. 

Women or people with more feminine energy in particular are more inclined to believe that if a relationship isn’t working, it means we’re not working hard enough on it. Often, the opposite is true: the person you’re with might not be doing their part.

So where does this leave people looking for a healthy relationship?

Doing the work to find someone who’s ready to do the work with you and doing the self-work to be a healthy partner for them in return.

How To Know if Dating is WORTH The Hassle

You asked if you “should” date. That means you’re undecided — and that’s when dating is going to feel like a hassle.

So how do you know if dating is worthwhile?

You’re in your fifties with two younger daughters and a grandbaby. I’m going to take a wild stab in the dark and say you’ve probably deprioritized yourself for a long time. That’s a common mom thing.

My questions to you are: is it worthwhile now to prioritize yourself and your own happiness? And would a quality guy add something meaningful to your life that’s missing?

If you feel like you should be dating because of societal expectations, then fuck that. If you’re happy on your own, then by all means, mama, own that solitude. It can be such a powerful statement to your daughters that you don’t need to date to be happy.

But you know what’s an equally meaningful statement?

Pursuing your own happiness.

Figuring out what that looks like is definitely worth the hassle.

How To Date And Protect Yourself and Your Family

We need to talk about scripts and boundaries.

We’ve absorbed hundreds of unhelpful scripts about dating and relationships. Like the idea that men won’t be attracted to women without breasts. Like the idea that you have to introduce your family to the person you’re dating … or something’s wrong.

What if I told you that you could completely erase any “should” you believe about dating and relationships and start from scratch?

And yeah, this is work. But it’s also how you can find freedom and joy.

If I were you, one way I would vet people would be to set a boundary and not introduce them to  your daughters and granddaughter for MONTHS. They have to earn that shit. And if they feel hurt about this boundary, then they’re not worth being in your life.

Set similar boundaries about having their friends around. In fact, it’s totally fine for you to say you NEVER want their friends to be around your daughters. 

When women and queer folks put out foot down about who is in our life and how, we’re doing powerful justice work. We’re chipping away at the patriarchy.

And I have more good news for you.

You’re in your 50s with kids!!!

Wait … why is that good news you ask?

Because you’re past the point of trying to build this cookie-cutter life with someone. You’ve made your family. You’ve built a life for yourself. You know what comes next???


If you want a lover you only see when you fly to St Thomas or rent a cabin for romantic getaways … you can do that! 

If you want a partner that has his own house and you live with him 2 days a week … that’s possible!

The real trick is finding someone for whom your ideal reality roughly matches their own.

Will it require some compromises? Of course. That’s being in relationship with someone. But what’s different is that you’re experienced enough to know what’s worth compromising on and where to stand your ground.

Attracting the Right People

One more important point. When you say you attract men that think you’re lonely and you tell them you’re “tittless” in hopes they’ll leave you alone …

You don’t owe these people anything, and it makes me wonder why you’re getting to the point where you’re talking to them about your breasts or lack of breasts in the first place.

You can always just say you’re not interested and leave it at that. And it takes practice rejecting people. But it’s typically the best approach to just be clear and concise.

But if you’re engaging in dialogue with them, maybe you are looking for something. Perhaps validation that you’re still attractive or desirable. 

I think the only way to attract the right people is to be clear about what you want.

Maybe it’s woowoo and an energy thing.

Maybe it’s just that the more you know what you want, the easier it is to spot.

But I believe if you can answer that question for yourself, you’ll find it.

Featured image by Esther Ann.

Jera writes about sexuality, spirituality, and social justice. They are the author of Just the Tip, a queer-friendly, sex-positive, relationship advice column and the editor of Sacred and Subversive,...