10 Faqs About Dating Over 50

When I sat down to write this, my brain went into overdrive. TEN FAQs? Only 10?

Let’s just say the original list looked more like the Cheesecake Factory menu – 50+ questions deep. After three cups of coffee and some ruthless self-editing, we’re down to 10 of the most common, most relatable, and yes, sometimes hilarious questions I hear every week.

After all, I’ve been doing this for over 30 years – started in my 20s – and every week, I talk to clients who ask the same big one first:

“Am I too old to date?”

Spoiler: You’re not.

Where I Got the Idea for This List

But before we dive into the FAQs, here’s what inspired this list – all in the past two weeks:

A. Boulder, Colorado, Family Weekend

My daughter (a junior) shares a house with seven girls and one bathroom. I went in to brush my teeth and was intercepted by Alana, whispering, “Andrea, can you come in my room? I need to ask something.”

She shut the door and said, “I like two guys and I’m dating both. Is that wrong?”

Me: “Do you want me to answer as your friend’s mom or as a dating expert?”

Her: “Expert.”

(And thus, another coaching session was born.)

B. Hiking the Flatirons

A woman I just met confessed mid-trail that she’s thinking of leaving her husband – who’s walking five feet behind us. Enough said.

C. Dinner with Friends

After a few glasses of rosé, the single woman at the table blurted, “I’m terrified of rejection. Should I even try dating again?”

My 10 FAQs

See what I mean? Dating questions come at me from all directions – bathrooms, hiking trails, dinner tables – so here are the 10 most common FAQs about dating after 50.

1. Am I Too Old to Start Dating Again?

Absolutely not. It’s not about age, it’s about attitude. Optimism is way more attractive than any filter.

2. I’m Confident in My Career, My Friendships, My Life – So Why Do I Feel 16 Again When It Comes to Dating?

Because dating confidence comes from practice, not theory. You didn’t learn your job overnight, and you won’t master modern dating without a few reps.

3. Where Do I Even Begin?

Jump in. Don’t “dip a toe.” Give it a 3-month commitment. Dating isn’t like yoga – consistency beats flexibility here.

4. Is It Worth Paying for Premium Memberships?

Yes. You want skin in the game – and you want your matches to have it, too. Free apps are great for window-shopping, not relationship-building.

5. How Soon Should I Meet Someone in Person?

Within a week. Period.

Texting marathons kill chemistry. Real connection happens in voice and body language, not in blue and gray bubbles.

If they keep delaying the meetup, they’re either unavailable, nervous, or not serious – all three are time-wasters.

6. Is It OK to Date More Than One Person at a Time?

Early on? Absolutely. You’re gathering data, not getting married. Compare, don’t confuse. Once something starts feeling serious, be honest and narrow your focus.

7. What If I Don’t Feel Sparks Right Away?

We’re not 18 – and thank goodness for that. Sparks are fun, but comfort, curiosity, and compatibility are keepers.

Sometimes chemistry is instant… and sometimes it’s a slow burn that sneaks up on you. But if it’s not happening by date #3 or #4, it’s probably not going to.

8. How Can I Tell If Someone’s Genuinely Interested – Not Just Passing Time?

Watch for consistency, not charm.

“Let’s get together sometime” = lazy.

“Are you free Thursday?” = intent.

Consistency is the new sexy.

9. What If I Have Zero Interest in Marriage Again?

Then don’t.

You get to redefine what partnership means now – companionship, travel, laughter, shared playlists, not joint tax returns.

10. How Do I Make Dating Fun Again Instead of a Chore?

Drop the outcome obsession.

Every date is a story, not an audition. Go in curious, not critical. When you lighten up, your energy shifts – and people feel it.

Bonus Truth Bomb

Fun people attract fun people.

Bored people attract… Netflix.

Ready to make dating fun again?

Let’s chat. Book a free 15-minute call with me — we’ll see if you’re ready to jump in, and if I’m the right coach to help you do it right.

Let’s Have a Conversation:

What are your questions to a dating coach? What would you like to know that puzzles you about online dating?

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