Come Along for the Trip You’ve Been Putting Off

Some trips are meant to be a little reckless. The weekend you’ve been teasing yourself with. The getaway that feels too indulgent alone. That vacation you keep talking about — and never book — because the fun doubles when someone delicious is packing beside you.

Pack the suitcase. Leave the solo act.

I’m not a polite guest for one dinner. I’m company for the whole adventure: wherever you’re headed, however long you’re staying, the kind of itinerary that gets better when someone is willing to say yes. Think easy mornings and unhurried evenings — and yes, the things that don’t usually match the résumé. The rollercoaster. The zoo. The game you’ve always wanted seats for. Sometimes a gentleman wants something a little out of character for his stature, and that’s half the thrill. Travel light. Stay discreet. Look like trouble in the best way.

Your trip. My company.

Long weekend, week abroad, beach, mountains, fly-me-to-you wherever the whim lands — we shape the days around what you actually want to do. Tell me the destination, or the one you’ve been too shy to say out loud. Bring the agenda you already have, or leave a little room for impulse; either way, I’ll meet you there. First note stays private and clear; then we see if the timing (and the chemistry) feel right.

If you’d rather not fly solo, Request Time is where we start. I’m curious where you’ve been wanting to go — and what you’ve been waiting for.

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Your Plus-One for Dinner, the Show, or the Night Out

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What to Expect from Daily Arrangements