27. Brunch With Friends
A variation on 26. Ask 5 friends to brunch with a Plus One. Have everyone bring their favorite breakfast thing. Or if you can afford it, ask for requests and make it all.
On New Year’s Eve 1999, I invited people over at asked each one what their favorite food was. I made it all, from cheesecake to sushi to pasta with sausage. Guests brought all the champagne and it wasn’t expensive at all.
After dinner, we watched everyone’s favorite movie scenes of all time, which they’d brought cued up on VHS.
28. Ice Cream
Go to a famous place where you can get wacky flavors like goat cheese brownie or burnt sugar ice cream. Or make it at home from fresh peaches. Or walk to your favorite neighborhood place and people watch while you eat.
Ice cream is always a good, low-key, cheap date. It’s good for when the small gesture is called for.
29. Ethnic Dives
Some of my best dates have been in restaurants that are foreign and cheap. Sitting on the floor and eating Moroccan basteeya or scooping up food with Ethiopian injera are two highlights of cheap eats dates that I recall fondly. The idea is to make dinner out a bit of an adventure. Try something different. Have a shot of grappa. Or try sea urchin in a shot glass. Push the boundaries with someone – you’ll bond over the experience.
30. Family Event
Once the relationship is established, people like being introduced to family. Don’t hesitate to ask a date to a family barbecue, wedding, christening or dinner. I confess I did have one disastrous date of this kind.
Joe Hillenbrand once asked me to his aunt and uncle’s for Christmas Eve. He had no parents, and played the pity card very effectively, which was necessary because he often abandoned his dates in the middle of the evening. I figured that wouldn’t be possible at a family dinner, so I said OK. We had to travel about 20 miles.
Shortly before dinner, Joe excused himself and I figured he was going to the bathroom. He didn’t come back for quite a while. Finally, his uncle went to investigate and returned to report that Joe had apparently left. He had left the premises, and me sitting there with his relatives. He never came back, and his uncle had to drive me home, but made me stay for dinner first.
Worst Date Ever!
In closing, I’ll offer some general guidelines about things to avoid.
1. Don’t go to malls. Shopping in general is no fun on a date. I don’t even like going to craft fairs, because there’s just pressure to buy stuff. Window shopping in the city can be OK, but personally I’d rather walk around the old colonial townhouses than stroll down the street and look in the windows at Tiffany’s.
2. Don’t bring a date to something that he or she is unlikely to be interested in. If you have an esoteric interest like historical war reenactments, that’s great, but don’t drag your date to the newest musket show at the local armory. I once made a guy walk through an exhibit of girls’ embroidery samplers and he was really out of place and bored. Save that for when the other person is in too deep to turn back.
3. Finally, I’m not a big fan of coupons being whipped out on a date. I’m sorry, I love Groupon as much as anyone, but I’m not going to treat someone with a Groupon. It seems stingy even though it’s perfectly rational.
The same goes for inviting someone out for dollar sliders or dollar drafts. Once you’re in a relationship, by all means. I just think watching pennies too carefully early on is a red flag, so why raise suspicion? I’d rather be asked out to fly a kite than to the twofer special at my local falafel restaurant.
The key is effort and creativity, which are always appreciated. Hopefully. If not, no second date.
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