You’ve been matched with someone for a SitByYou companionship session.
Now comes the question:
What should you actually do together?
The answer can be surprisingly simple.
A great companionship session doesn’t require an elaborate activity, a packed schedule, or constant entertainment.
Sometimes the best sessions happen over a cup of coffee and a good conversation.
The goal isn’t to keep someone busy.
It’s to spend enjoyable, meaningful time together.
Here are some ideas to get you started.
1. Start With a Conversation
Never underestimate a good conversation.
Ask about interests, experiences, favorite places, movies, music, food, travel, hobbies, or whatever naturally comes up.
Don’t treat it like an interview.
Let the conversation develop naturally.
And remember: being interested is often more important than being interesting.
2. Share Coffee or Tea
Some of the best conversations happen around a table.
Make a cup of tea or coffee, sit down, and talk.
Simple can be wonderful.
3. Play Cards or a Board Game
Cards, chess, checkers, Scrabble, or another favorite game can give you something fun to do while you talk.
Ask your companion what they enjoy rather than automatically bringing your own favorite.
They may even teach you something new.
4. Watch a Favorite Movie
Ask each other about favorite movies.
You could watch an old favorite, discover something new, or even start your own little movie tradition.
And half the fun may be talking about it afterward.
5. Listen to Music
Music can be a wonderful way to connect.
Ask:
“What music do you love?”
You may discover favorite singers, concerts, songs, or memories connected to particular music.
You might introduce each other to completely different generations or genres.
6. Share a Hobby
Maybe one of you loves:
- Gardening
- Knitting
- Drawing
- Photography
- Cooking
- Crafts
- Collecting
- Writing
- Sports
- History
Shared interests can make companionship feel natural.
And you don’t have to already share the same hobby.
Sometimes it’s fun to learn about something another person loves.
7. Take a Walk
When appropriate for both people and the setting, a walk can be a simple way to spend time together.
Walk through the neighborhood.
Visit a park.
Explore a garden.
Or simply enjoy being outside.
The activity doesn’t need to be strenuous. The point is enjoying the time together.
8. Look Through Photos
Photos are conversation starters.
Travel photographs, family pictures, old neighborhoods, weddings, pets, holidays—one picture can lead to an hour of stories.
And remember to listen.
The story behind the photograph is usually much more interesting than the photograph itself.
9. Read Together
If you both enjoy reading, share an article, short story, poem, magazine, or book.
You could even choose a book and read it between sessions, creating your own two-person book club.
10. Cook Something Together
If you’re meeting in an appropriate setting and cooking is permitted and safe, making something simple together can be enjoyable.
Perhaps you both have favorite recipes.
You might even come from different cultures and teach each other something.
Cooking naturally creates conversation—and you get to eat the result.
11. Explore Somewhere New
Companionship doesn’t always have to happen sitting at home.
When appropriate and mutually agreed upon, you might visit:
- A museum
- A café
- A park
- A library
- A community event
- A farmers market
- An art exhibit
- Another suitable local activity
Sometimes companionship is simply having someone to go somewhere with.
12. Learn Something From Each Other
Every person knows something you don’t.
Maybe your companion knows how to play chess.
Maybe you know photography.
Maybe they can teach you a few words in another language.
Maybe you can introduce them to a new technology.
Companionship can go both ways.
13. Create Something
Draw.
Write a short story.
Make a scrapbook.
Try a craft.
Create a playlist.
Plan an imaginary trip.
Creativity gives you something to focus on together—and often leads to unexpected conversations.
14. Ask What They Want to Do
This may be the most important idea on the entire list.
Ask.
“What would you enjoy doing today?”
Don’t assume someone’s age, health, background, or circumstances tell you what they’ll enjoy.
One person might want a quiet afternoon.
Another might want to get out and explore.
Let the person you’re spending time with have a voice in how you spend that time.
15. Sometimes, Do Nothing
Not every moment needs an activity.
You don’t have to fill every silence.
You don’t need to arrive with entertainment.
Sometimes two people can sit on a porch, listen to music, watch the world outside, or simply talk when there’s something to say.
Being comfortable enough to simply be together can be companionship too.
The Best Activity Is the One You Both Enjoy
There isn’t one perfect companionship session.
What matters is getting to know the person you’re spending time with.
Pay attention.
Ask questions.
Remember what they enjoyed last time.
Try something new occasionally.
And don’t put pressure on yourself to manufacture a meaningful moment.
Often, those moments happen naturally.
At SitByYou, we believe companionship works best when two people aren’t simply matched by time and location, but have an opportunity to connect through personality, interests, experiences, and the things they enjoy.
Because a great companionship session isn’t about how many activities you planned.
It’s about whether you enjoyed the time you spent together.