Why I Went On A "Date" 1 Day After My Surgery

Two days ago, a surgeon removed a polyp from my uterus.

📸: Earlier photo from bloodwork.

Yesterday morning, per doctor’s and nurses’ orders, I was walking laps around my apartment to keep my blood circulating. I was also eating healthy, drinking lots of water, checking in with friends, and otherwise making sure that I’m taking care of myself.

That evening, a day after surgery, I put on real clothes, left the house, and met an Italian man. I took a Bolt to reduce any walking, and skipped alcohol because my body is healing.

Still taking care of myself, I figured, if I have to eat dinner anyway, might as well do it in the company of another person.

Nothing was at stake because nothing could go wrong.

This was our second “date,” if you can call it that. I’d already clocked that this guy was never going to be anything more than platonic.

Honestly, I went on the date because I don’t have as many straight male friends anymore. The married ones’ wives (and the dating ones’ girlfriends) don’t necessarily want their guys gaining a new woman as a bestie. The single ones sometimes confuse my kindness for interest, so I lean toward backing off.

So, this date was low-maintenance male company.

In the end, I paid for my own meal, then I went home early. The next day, today, we texted each other and agreed: We just didn’t click.

I’m healing well, by the way. No pain, no complications, and biopsy results should arrive in a couple of weeks. (I’m also staying home for the remainder of the week.) Just sharing the update, not because anyone needs the whole story. Just closing a loop.

Besides, I joke that 50s+ dating is just a bunch of old people scheduling dates around medical procedures. 😂 So, all of this has me thinking about men at my age in general.

Newly over 50, I’m also somewhat newly discovering men at this age, too. Relationships with them, whether platonic or otherwise, have a different texture. Having likely already encountered marriage, divorce, or widowhood, there are often faint traces of another woman’s presence and absence in their aura. Sometimes the trace is literal: exes or children. Sometimes it’s figurative: the grief and emotional scars that arrive as a consequence of being human. Maybe they’re caring for an aging parent. Maybe they’re carrying something they haven’t named yet.

I know I’m certainly a different woman than I was in my 20s. My hair is greying, though you can’t tell because I color it. I weigh more. I’m less likely to wear makeup or fuss with myself too much. In the battle between heels and cobblestones, cobblestones win, so I almost always wear flats.

I’m literally and figuratively stripped down to the most natural version of myself, and that includes my preferences. I’m not going to disagree with a man about feminism, racism, my body, or pretty much anything else major. We’re either on the same page or we’re not, and I’m not interested in pulling anyone to my side or moving toward theirs. It’s called compatibility. I’ve been thinking deeply about the world for half a century. Chances are, they have, too.

Either way, men at my age tend to carry more into their friendships and relationships than just dating preferences. Which is exactly why I find them so interesting.

I’m fascinated by people in general, including men. Whether it’s a new friend, your dad, a potential partner, yourself, or anyone else, here are 50 questions to help you get to know the 50+ man in your life a little better. Or, how about this: If you’re not yet 50, think about how you’d want to answer these questions when you reach that age, and what choices you’d need to make now to be comfortable with those answers then.

These questions are about tapping into levels of emotional awareness, self-reflection, and vulnerability. The goal is to stoke curiosity, not to freak anyone out.

Happiness

• What did fun look like for you before life got more complicated? What does it look like now, and how do you feel about the difference?

• What makes you laugh the hardest?

Physical connection

• How do you feel about your body and sexual functioning at this stage of life, and how does that affect how you show up with someone new?

• What does physical affection look like for you outside of sex?

• How important is sex to you in a relationship right now, and how does that show up?

Friends & social support

• Who do you call or text first when something good or bad happens?

• Who are your closest friends, and how often do you actually see them?

• Has your social circle changed a lot in the last 5–10 years?

Relationship past

• How did you contribute to your last relationship (or marriage) ending?

• What did you learn about yourself from your last relationship that surprised you?

• What’s something you wish you’d done differently in a past relationship?

• How’s your relationship with your ex(es)?

• Tell me more about one person in your past you feel like you can’t really let go of. What would it mean to you if you did?

Relationship future

• What does loneliness feel like for you these days?

• What do you actually want companionship to give you?

• At this point in your life, are you more interested in finding a partner, or more interested in not being alone? For you, what’s the difference?

• What do you know now about love that you didn’t know at 25?

• What are you no longer willing to tolerate, and why?

• What does a good partnership look like to you at this stage of life?

• What are you hoping your next relationship adds to your life that you’re not currently getting?

Family of origin

• What was your parents’ marriage like?

• What did you learn about relationships from watching your parents?

• Are you close with your family now?

Money & security

• How do you think about money? Are you a spender, saver, or something else?

• Has money ever been a source of conflict in any of your past relationships?

• What does financial security mean to you at this point?

Purpose & work identity

• Do you feel like you’re doing what you’re supposed to be doing?

• What do you want the rest of your life to look like, generally speaking?

Fear & self-protection

• What would make you want to run from a relationship, even a good one?

• Which feels harder for you right now: opening up to someone new, or trusting that your next relationship will last as long as you’d like it to?

Emotional regulation & conflict

• What does a disagreement with a partner usually look like for you?

• Do you need space during conflict, or do you want to talk it through right away?

• Tell me about the last time you were really frustrated with someone. How did you handle it?

Communication & trust

• Do you find it easy or hard to trust people early on?

• When something’s bothering you about someone you’re dating, do you prefer to bring it up right away or sit with it until you feel comfortable?

Kids (if applicable)

• Do you have any children? (if “no” → “Did you ever?”)

• How do your kids factor into how you think about dating?

• What would it mean for you to introduce someone new into that part of your life?

*Note: I like this question verbatim. “Do you have any children?” tends to surface stepchildren, kids they’re raising as their own, and those who’ve passed away. Asking “How many children do you have?” can short circuit to a quick answer like “none.”

Life logistics

• What does your living situation look like right now?

• What does a normal week look like for you?

• What’s your relationship with alcohol and drugs?

Growth & self-awareness

• What does emotional maturity look like to you now, compared to when you were younger?

• What’s something a past partner said about you that stuck with you?

• Have you ever been to therapy or done any kind of self-reflection work?

• What do you still find yourself working on personally?

Time

• What matters most to you in how you spend your time these days?

• How much of your time is actually free for yourself, versus tied up with work, kids, or other obligations? Subtracting all of that, how much time do you realistically have for a relationship?

Identity & life stage

• Who are you now that you weren’t ten years ago?

• What matters to you now that didn’t used to?

• What are you hoping to build or experience in your next chapter, and how do you see a partner fitting into it?

Forward-looking

• If this doesn’t work out, what do you think you’d want to know earlier next time?

• What would you want someone to understand about where you’re starting from right now?

By the time we reach 50, we’ve lived (and known people!!) for multiple decades. Tread lightly. Grief and past relationships deserve space, and sometimes ongoing emotional healing. Ditto for teasing out the difference between someone being “lonely” and filling a void, versus “ready” and seeking a partner.

Don’t ask all fifty questions. Pick three to five and let the rest of the conversation unfold naturally from there.

In the end, the Italian didn’t matter. We didn’t even click on a platonic level, even though the right ingredients were in the mix. Physical and intellectual attraction can kindle on the surface, but depth is where the magic actually happens.

All of this leads me to a much less platonic corner of my life.

Truth be told, my heart and emotions are being tugged in a different direction. I’m feeling kinda into someone right now. It’s still early. Maybe it turns out to be something, maybe nothing. But this kind of connection doesn’t happen all the time & I like him. So, I’m feeling hopeful, excited, and enjoying the process.

Tiny, Private Love Letter is written by Twanna A. Hines, an obsessed observer of how we love, learn, leave, and find our way through this world. When you subscribe or upgrade, you’re supporting independent writing and helping offset the cost to produce the work you’re currently reading.

Twanna A. Hines, M.S. is an American entrepreneur and award-winning sexual health educator. She is founder of FUNKY BROWN CHICK, Inc., a social impact consultancy serving nonprofits, foundations, B-Corps, and international organizations. She has appeared in The Guardian, NBC News, Al Jazeera, Fast Company, and 25+ other outlets; she has been covered by The New York Times, CNN, Cosmopolitan, Essence, Vox, and 50+ additional media outlets. She has been called “a gifted storyteller” by The Washington Post. See more at: twannahines.com.