The Envelope

Choose Your Pace. A quick guide.

If you want the version of me that’s unhurried, playful, and the most present, give us enough time to settle in. The right pace makes everything better: the conversation, the chemistry, the ease.

New to me: 3-4 hours is the simplest first date. Enough time for nervousness to melt, but not so much time that there’s pressure. And you can always extend the time!
The real magic: 4-6 hours is where we stop checking the time and start actually enjoying each other. If you prefer to start the date later in the day, then an overnight might fit your style!
Short and sweet: 90 minute dates are best for those with truly tight schedules who are looking for a quick reset from real life.

24 Hours. A Full Escape.

$9,000 ($5,000 each additional 24 hrs)

We disappear for a whole day and let the world handle itself. We eat, we nap, we flirt, we roam, we come back, we change outfits, we forget what time it is on purpose. This one feels like a tiny, private universe: part adventure, part cozy, part “how is it already night?”
Ideas: a Hoxton staycation with brunch and a rooftop dip, then Lazy Bird after we’ve ruined our sense of time; Logan Square for thrift shops, used bookstores, and tacos; or a beach day with sandy toes that somehow turns into a bubble bath feast back in bed.

Overnight. The Dream Loop.

$6,400

Fall asleep close. Wake up sweeter. Overnight is all the good parts: the late-night snacks, the 2am giggles, the soft quiet, and that morning moment where you realize you don’t have to rush back into your life yet.

Ideas: diner fries and milkshakes at midnight before we disappear back upstairs; a slow walk along the river with little pauses that turn into longer ones; takeout in bed with no alarms and a very un-serious morning.

6 Hours. The In-between Dream.

$4,200

Six hours is where everything unclenches. No time pressure, no “what’s next,” no performing. Just a full evening to exist together: playful, present, and unhurried.
Ideas: bowling or mini golf, then collapsing into robes with snacks; golden hour in Lincoln Park; late-night Pequod’s in a suite, pretending the city doesn’t know where we are.

4 Hours. The Cozy Date.

$3,200

Four hours is the shortest length that still feels like a whole night. We can go out for something easy and fun, or stay in and make the room feel like ours.
Ideas: dinner and drinks at an upscale restaurant or Thai takeout on a hotel bed with the outside world politely ignored.

3 Hours. The Slow Burn.

$2,600

Three hours gives us room to warm up properly. Conversation, snacks, flirting, pauses, circling back, that “oh… there you are” feeling when chemistry settles in.
Ideas: a night walk with intentional detours; splitting something messy and feeding each other bites; music on low while the vibe quietly shifts.

2 Hours. The Spark.

$2,000

This is the “quick, but we actually get comfy” date. Enough time for nerves to fade, for laughter to show up, and for the evening to feel like something real, not a sprint.
Ideas: a coffee or drink that turns into a slow, private reset; a curated playlist and a room we make ours for a little while.

90 Minutes. The Warm Hello.

$1,600

A short and sweet hello. Great when we already know we like each other, or when schedules are tight and you want a little fun without making a whole night of it.
Ideas: a quiet room and letting the city noise fade while we focus on each other.