How to Let a Man Know You’re Interested


First things first: The people have spoken. Everyone’s sick of promiscuity, at least as a discussion topic. Commenters have been saying so all week, and last night I dreamed that SlutWalkers stormed my home like it was the Bastille. So we’re taking a holiday from discussions of a woman’s number, and whether guys like, date or marry sluts. The truth is, they will or they won’t, no matter how much we discuss it here. Suffice to say that we’ve probably said everything relevant, at least for now.

So! Welcome to the fun and interesting Hooking Up Smart, where all the guys and gals are above average!

A while back a reader reminded me that I’d promised a post on great cheap dates. I love cheap dates, even now. I’d much rather cook chili with my husband than go to an expensive restaurant.

Some cheap dates are great for the early stages of a relationship, or when you’re hanging out with a friend who has Heavy P (otential). Many of them can easily be initiated by a woman, and are the perfect way to reciprocate when a man has taken you out. Some work well in groups, others are perfect for two. There’s lots here for daytime, too, which is perfect when you get to that stage where you’re spending 24 hours together sometimes.

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A list of cheap dates

Here is a list of cheap dates I’ve been on, and why they were so enjoyable.

1. Flea Market or Antiquing

It’s fun to look at junk that reminds you of your childhood or past. I almost always find something inexpensive to buy. Once I bought Look magazine from 1939 with a portrait of the Duke and Duchess of Windsor on the cover, with advice on “How to Crash the Windsor’s Set.” That magazine still sits on my coffee table. Another time I bought a bunch of Girl Scout badges from the 60s and stuck them on my bulletin board. Conversation is easy when exploring this way.

2. Book Reading

Go to a book reading for an author you both follow. Then you can discuss their writings over a drink or dessert as you enjoy the rush of having been in the same room with someone you truly admire.

3. Drive-in Movie

If you live near one of the remaining drive-ins, go with pillows and blankets and snacks. Or just make out. Warning: cars aren’t made for drive-in comfort any more. No big bench seat in the front, and getting in the back is no good because the headrests block the view. I saw a James Bond film on a date, though, and it was really fun.

4. Revival Movie House

Mr. HUS and I saw most of the Hitchcock films in the theater when we were dating, and they were such fun. Those dates of nearly 30 years ago remain fresh in my mind. We still quote them all the time. “Judy, please, it can’t matter to you.” “Fred, that feed you sold me is no good.”

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5. Rent a Boat

I leave near a beautiful glacial pond in the city. You can rent a rowboat or sailboat there for $10, but hardly anyone does. It’s a lovely way to spend an afternoon on a lovely day, very romantic.

6. Oyster Festival

Or whatever festival. The Wellfleet Oyster Festival every October is fun, filling and cheap. Watching those old salts shuck like crazy is amazing. There are still bits of old time Americana around, and it’s fun to see them.

7. Botanic Gardens or Arboretum

Perfect in the early stages of love, when you just want to hold hands and moon over each other.

8. Retro Dining

I recently went to a Sinatra brunch at Lucky’s Lounge and it was great, with live music. Diners are always fun too.

9. Play Tennis

I don’t play, but I’ve had fun just volleying at a local community court. If one of you plays, you can teach the other (This tends to work better if the male plays. Just saying.)

10. Art Museum

I once went to an art museum on a day when it was so snowy that classes were cancelled. It was eerily empty which was kind of cool. Afterwards we got busy in the car, the only one in the parking lot, while the snow came down fast and hard. That was memorable.

Bank of America funds free museum days on the first weekend of every month in many locations across the country, so check. I recommend February.

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11. Shop For Food Then Eat It

I’ve done the Farmer’s Market, an Armenian grocery, Chinatown. The key is to share the food together afterward. You don’t want to be going on a date to the Farmer’s Market where you each take home your own mangoes. Charm your date by buying them field flowers like zinnias or sunflowers.

12. Bike Ride

Rent a tandem, it’s really fun. Or go on a nice long ride on a dedicated bike trail. You can have lunch somewhere, then head back.

13. Scavenger Hunt

One of the most fun dates I ever had was going to a birthday party scavenger hunt. We were put in teams, and hilarity ensued. What a great way to meet people! Why not think about planning one, and inviting a bunch of people to bring a date?

14. Sledding

Best in a group, but taking a walk immediately after a snowstorm is really fun for two. Plan on hot alcoholic beverages to follow.

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15. Shakespeare in the Park

Bring wine and come early. I had a great time seeing Much Ado About Nothing on a date.

16. Poetry Slam / Open Mic Night / Improv

Usually good for laughs, and often a way to support a friend working on material. It’s a feel good experience all around. Ditto for going to see a friend act in a play or play in a band.

17. Art Galleries

When Mr. HUS and I were living in NYC and broke, we used to walk over the Brooklyn Bridge and all the way uptown to art galleries. We tracked the shows in The New Yorker, and got pretty good at following artists we liked. I can’t say that any gallery owner ever looked pleased to see us, but hey, who cares. Usually, we’d finish up by having a bite or a drink somewhere, then spring for the subway to get home.

18. Driving Range

Golf is addictive. If you play golf, help someone improve their stroke. (Bwahahaha) Again, this may work better with men in the teaching role.

19. Fireplace Picnic

On a cold winter’s night, lay out a picnic in front of a roaring fire. Be sure you are on a comfy blanket, because this always ends in sex. If you’re not there yet, try Scrabble. It’s really fun to play a board game with a date, and you learn a great deal about a person that way.

20. Hike

I don’t mean a namby pamby perambulation. I mean an endorphins-producing work session with a clear goal, like a summit. Climb to the top of something and look at the view. The world seems wondrous at such moments, and that will do wonders for your date chemistry.

21. Break Out the Michelin Guide For Your Own City

Be a tourist in your own city. I don’t mean going to the Empire State Building, though that would be cool. I mean going into a neighborhood and exploring it fully. Read the history, look at the architecture and eat the food.

22. Beach

Going to the beach in general is a pretty good date. It’s especially romantic off-season. There’s something about going in a hooded sweatshirt that is so much fun. Bring your dog if you have one. If not, get a dog.

Off-hours is also good. I’ve had dinner at the beach when everyone had left, I’ve gone for a walk along the water’s edge when the moon was full, and I especially like going early on a Sunday with coffee and the paper.

23. Apple Picking

Go to a farm in the fall and get apples. Come home and make apple stuff.

24. Outdoor Concerts

Often free, a great way to enjoy music in a group. People start dancing, there’s a great vibe. Avoid the massive venues for dates – I’m talking about small, local gigs. Our local art museum has these in the courtyard all summer.

25. Camping and/or Kayaking

I’m past the age where I’ll sleep without indoor plumbing nearby, but I had many great dates back in the day river rafting, kayaking (the flat kind that doesn’t roll over) and camping. It’s a great way for a woman to show an outdoorsy guy that she’s game for doing what interests him.

26. Watch the Game

Invite someone over to watch a specific sporting event. Invite some other people too. Prepare food in keeping with the theme. Serve alcohol.

Omaha encounters 

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In closing

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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Datum laatste wijziging: 08-11-2022

Aanmaakdatum: 08-11-2022

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