"Kidnap" your date before they usually get up, preferably sunrise, (depending on the activity planned) and only let them put on their shoes with their pajamas, (or maybe slippers since you can always pre-purchase some fuzzy animal ones!) If your date is not comfortable heading out in their night clothes, use a three minute change rule or offer a long coat to go over their pajamas.
Have a picnic breakfast at a nearby park or quiet area (donuts, bagels, fruit, juice, or maybe bring champagne for mimosas if you are over 21 and alcohol is allowed there). Your date can end there of course, but you can consider adding on depending how daring your "victim" is. I don't suggest taking a very conservative or quiet person to the mall in pajamas, since that can turn the dream date into a nightmare, but if they are adventurous maybe hit a movie or drive around and find the perfect house you would want to some day wake up in.
Make sure to get permission beforehand from any roommates or parents.
Have a picnic breakfast at a nearby park or quiet area (donuts, bagels, fruit, juice, or maybe bring champagne for mimosas if you are over 21 and alcohol is allowed there). Your date can end there of course, but you can consider adding on depending how daring your "victim" is. I don't suggest taking a very conservative or quiet person to the mall in pajamas, since that can turn the dream date into a nightmare, but if they are adventurous maybe hit a movie or drive around and find the perfect house you would want to some day wake up in.
Make sure to get permission beforehand from any roommates or parents.
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