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A trivia night with friends is always a fun time, especially if a group date is more your style.

Sport your cutest button-up skirt and off-the-shoulder top. Share your favorite bar or coffeehouse, and let him share his.

Why, with so many dating apps making it easier to meet people, has it become increasingly difficult?

I believe that because it has become so easy to find, talk to, and meet up with someone, there is little risk involved and therefore less effort to create real connection.

Check calendars for convention centers, performing arts halls, parks, social clubs, and the like. Whatever you find, you'll have plenty to talk about.

It could be the municipal marching band, an amateur piano recital, or a choral concert.

Matinee shows have it all: cheaper tickets, emptier theaters, cleaner floors. Bonus points if you haven't seen the movie he picks and vice versa. Plus, playing games is a great way to bring out your date's playful, competitive side.

It can be as simple as coloring pictures or as complicated as making something for your apartment.

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You pack the main course and he packs the sides, or vice versa. If the pool isn't your thing, the hot tub is another—steamier—option. This could be difficult if you don't have a fire pit, but sitting around a fireplace is similar. Have a drink at your favorite place; have another at his.

Go during the week for deals on drinks, shoes, or games.

For a casual date, challenge your partner to a round of "Jeopardy" or "Wheel of Fortune"; whoever loses pays for snacks. You'll have fun cooking; and if it tastes bad, order takeout and laugh about it.

Find a museum with cheap admission and learn something! Whether it's a high school or community production, tickets are often inexpensive, the shows are fun, and the experience will spark conversation afterward.

Soup kitchens, food pantries, and animal shelters are all great places to give back and get to know your date.

Put your hair back (check out these 18 pigtail hairstyles for grown-ups) and throw on a cap, and you're ready to go.

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