A date night plan
Painting each other: a date with questionable proportions
Plan a relaxed portrait-painting date at home, with a simple supply list, five easy stages and prompts for your very unofficial gallery opening.
Is this the plan for you?
Time to allow
Allow around 2 hours, including setting up and clearing away. A pencil portrait can be a 30-minute version.
Budget notes
Use paper and pencils you already own for a no-new-spending version. Paint, brushes or canvases add to the cost; agree a materials limit before shopping.
These are planning suggestions, not live prices or bookings. The shorter and longer versions give you room to adapt the activity to your day.
Illustrative artwork; not a photograph of a tested outing.
Put two sheets of paper on the table and draw each other. That is enough to start. Pencils work; paint is optional. Choose one feature you like about your partner and try to get that into the picture, even if the nose ends up somewhere unexpected.
The plan below gives you a relaxed evening, but you can use the 30-minute pencil version if you want less setup. Keep the portraits private until the reveal, then explain one detail before handing them over.
Your supply checklist
Tick off what you have gathered, or print a fresh checklist. Ticks are for this page only.
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One sheet or canvas each, plus spare paper
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Pencils or suitable paints and brushes
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A table cover and something to protect clothes
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Water pots and a cloth if your paints need them
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A mirror only if you fancy checking how wrong the painting is
A 30-minute portrait date you can start tonight
Use two pencils, two sheets of paper and a timer. Here is a complete short version; no shopping trip required.
1. Minutes 0–3: each choose a detail to include, such as glasses, a favourite jumper or a familiar grin.
2. Minutes 3–8: sketch the head, shoulders and that one detail. Big shapes first; eyelashes can wait.
3. Minutes 8–20: add a background with a shared memory in it. A rectangle labelled “our first flat” is allowed.
4. Minutes 20–25: finish without peeking at the other picture. Write a title on the back.
5. Minutes 25–30: reveal both portraits and ask “which bit did you most enjoy drawing?” Put the supplies away together.
Make it happen
1. Set up a very forgiving studio
Cover the table, leave room for elbows and put materials where you can both reach them. Keep drinks away from paint water unless you enjoy an unnecessarily suspenseful evening. Choose a few colours rather than putting every tube on the table. Fewer choices make it easier to get started.
2. Choose the sort of portrait you want
Agree on a straight portrait, a favourite-memory scene or a gloriously exaggerated character. Ask each other what would feel fun and what would feel unkind. The joke should be the painting, not someone’s appearance. Pick one detail to include, such as a favourite jumper, a familiar expression or a tiny hobby-related prop.
3. Make a quick first version
Give yourselves five minutes on spare paper. Draw the large shapes first and leave eyelashes for another lifetime. This practice round gets the blank-page nerves out of the way. Swap a little encouragement, then start the main picture. If you are taking turns, agree an equal sitting time before the first brushstroke.
4. Paint, chat and leave room for surprises
Work for a comfortable stretch, then pause to move around and look at your progress. Talk about a memory, a place you would like to go or the story behind that jumper. You can keep the paintings secret until the end, but only if hiding a canvas does not require sitting in the corridor.
5. Open your two-person gallery
Give each painting a ridiculous title and explain one detail you enjoyed adding. Ask before sharing photographs of the results. Let paint dry according to its instructions, then choose whether to display the portraits, keep them in a folder or simply remember the evening. Put the supplies away together so the date does not end with one person scrubbing everything.
Make it work for you
Only half an hour?
Use pencils and one sheet each. Try three short rounds: a normal portrait, one drawn without looking down and one showing your partner as the hero of a completely imaginary film.
No paints or confidence?
Make a collage from coloured paper or old magazines, or draw each other as simple stick figures in a meaningful scene. The story you put around the person can do most of the work.
A quieter date
Sit beside each other with a reference photo you both approve. You can work without posing or maintaining eye contact, and reveal the pictures when you feel ready.
Before you begin
Use materials suitable for the surface and follow their labels. Protect furniture, allow ventilation if the product requires it and keep art supplies separate from food. Check that each person is comfortable being drawn and with any photo sharing.
Your unofficial gallery cards
Print these prompts, cut them out if you like and give each finished picture a label.
1. The title of this masterpiece is…
2. One tiny detail I wanted to include was…
3. This reminds me of the time we…
4. The artistic decision I am bravely refusing to explain is…
5. One thing I enjoyed about making this with you was…
These prompts are included when you print the plan and checklist.
A flattering portrait is lovely. A painting you both still laugh about next year has its own sort of value.
How did your date go?
Was a step unclear, or did you find a useful shortcut? Tell us the activity and what you would change.
Email feedback about this plan →Your email app opens so you can choose what to send. Please leave out private details, children’s names and photographs of other people.
Make choosing the date part of the date
Put a few possibilities you both like into a board and enjoy finding out which one wins. The sample game is an easy place to start.
A few more possibilities
Decorate each other a mug: tiny artwork for the tea cupboard →A pottery class for two hopeful makers and one unpredictable bowl →A couples photo shoot without the awkward engagement-poster poses →Published by Daniel Jenkins · Guide text updated 11 November 2026
The activity lists were supplied and edited for Deal or Date. Guides and illustrative artwork use AI assistance. They are planning suggestions rather than accounts of personal trips or product tests. Venue prices, entry rules and accessibility need checking with the place you choose.
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