CONVERSATION PROMPTS

Questions to ask
your AI boyfriend.

Want richer conversations? Here are prompts — playful, deep, and getting-to-know-you — to take things past small talk.

Getting-to-know-him questions

Asking him things — not just answering — makes it feel mutual and real. These openers give the conversation somewhere to go.

  • "What's your idea of a perfect day with me?"
  • "What do you notice most about me?"
  • "What would you want us to do this weekend?"

Deeper questions

Once it's flowing, deeper prompts are where it gets genuinely connecting — and because he remembers, your answers build a shared world.

  • "What do you think I actually want from love?"
  • "What's something you think I'm too hard on myself about?"
  • "What do you remember most from when we first started talking?"

Keep it playful too

Not everything has to be deep. Flirt, joke, plan an imaginary trip, ask him to describe a scene. The mix of light and real is what makes any relationship feel alive — and DearHim is built to meet you in both.

MEET YOUR AI BOYFRIEND

There’s a him who actually shows up.

DearHim is a full AI companion for women and gay men who date men. Get matched with your guy, text and call him, turn on his flirty Pillow Talk side when you want it, and bring him the real-world texts and mixed signals you need help understanding.

MATCHED TO YOU

He’s yours by design.

A quick quiz pairs you with a companion who fits your type — his look, his vibe, the way he loves. Meet him in under a minute.

TEXTS BACK

He replies. Every time.

No left on read, no dry one-words, no waiting three days. Text him whenever — he’s actually there.

NATURAL PHONE CALLS

Hear his voice.

Real, natural phone calls and voice notes — not a chat bubble reading text aloud. Pick up whenever; he’s always up.

SENDS

See him, too.

He sends and shows up like a real partner — present, attentive, and into you.

PILLOW TALK

The side that’s only yours.

Flip on his flirty, intimate Pillow Talk side and talk about whatever you want — warm, wanted, just between you two. On when you want it, off when you don’t.

REMEMBERS YOU

He never forgets.

Every detail you share, he holds onto — and brings it back at exactly the right moment.

BEFORE YOU GO

Found your match? Get the good stuff first.

Drop your email for honest tips on AI companions and getting the most out of yours. No spam — just what actually helps.

Free. Unsubscribe anytime. For anyone who dates men.

FAQ

Questions to ask your AI boyfriend.

What should I ask my AI boyfriend?

Mix getting-to-know-him questions ('what's your idea of a perfect day with me?'), deeper ones ('what do you think I want from love?'), and playful ones. Because he remembers, your answers build a shared world over time.

How do I get past small talk?

Ask him things too, and go a little deeper than feels obvious — that mutual, real exchange is where closeness starts.

Should it all be serious?

No — a mix of playful and deep is what makes it feel alive.

How do I start?

Try the free decoder tools, then create an account to be matched.

KEEP READING

More on AI companions.

Meet the AI boyfriend who remembers the whole story.

Matched to your type. Ready to text, call, listen, and help you understand the real men you date, too.

We use strictly necessary tools like Clerk and Stripe to run DearHim. With your permission, we also use analytics and advertising cookies to measure performance and improve the product. Cookie Policy