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Best of San Antonio

Milkshake date spots

A date is not complete unless you can share a milkshake together.

Based on 690 Opinions
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Updated May 2026
01
Burger Boy image 1
Burger Boy image 2
Burger Boy image 3
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Hamburger restaurant

Classic burger diner with spacious booths and an old-school vibe creates a noisy, fun atmosphere that draws locals, families, and late-night crowds. Clean, well-lit interior complements the dog-friendly policy with pup cups. Quick drive-thru service adds convenience to the experience.

Milkshakes come with every order and stand out for their rich flavor and creamy texture. Fruity Pebbles milkshake is a notable choice that adds a fun twist.

Staff show patience and double-check orders, making it easy to navigate choices together. Sharing a burger and trying the fruity pebbles shake adds a fun, casual touch to the experience.

People are saying

"These burgers are always fresh, juicy, and cooked perfectly."

"The milkshakes here are thick, creamy, and very tasty."

"I swear, the burgers and fries here are heaven-sent."

Good to know

1

The drive-thru is quick and efficient, especially before 5-6pm.

2

Prices range from $12-15 for a filling meal.

3

Expect no long wait times during peak hours.

02
Maple Waffles image 1

Small bakery with a cozy, family-run vibe and quaint interior filled with plants. Atmosphere feels warm and inviting, with kid-friendly areas and board games that create a relaxed, playful energy. Waffles and crepes are a highlight, served with care and quality.

Milkshakes here taste very good with a balanced banana flavor that complements meals well. They offer a variety worth trying on return visits.

Waffles stand out as a go-to breakfast item here, often paired with eggs and bacon. The spot draws couples looking for a simple, satisfying meal near home or on the way out of town.

People are saying

"I found the food here to be delicious and made to order."

"These waffles are huge, fluffy, and made with fresh ingredients."

"I thought the milkshake was very tasty."

Good to know

1

Parking space at Maple Waffles is limited.

2

The store is not wheelchair accessible.

3

The restaurant has limited dine-in space.

03
Peach Cobbler Factory - Alamo Ranch image 1

Small, clean dessert shop offers a casual atmosphere with friendly service and modern decor. Walls invite guests to write positive messages, creating a family-friendly vibe enhanced by music and games. The energy is welcoming and relaxed, perfect for enjoying phenomenal peach cobbler.

Milkshakes come in banana pudding, strawberry cheesecake pudding, and chocolate chip flavors. Staff often recommend the strawberry cheesecake pudding milkshake. These shakes pair well with cobblers and cookies.

Regular cobbler stands out as a sweet treat here. The service and environment create a relaxed vibe, making it a solid spot for a date night or family stop.

People are saying

"I found the cobbler here to be absolutely amazing."

"It's a perfect spot for a date night craving something sweet."

"I thought each milkshake flavor was amazing."

Good to know

1

The grand opening is on Saturday, August 24th.

2

UFC Fight Night events are shown during visits.

3

The establishment offers a wide variety of desserts.

04
Bee Nice Cream image 1
Ice cream shop

Ice cream shop offers homemade unique flavors with dairy-free options in a bright, clean, and spacious setting. The atmosphere is calm and kid-friendly, featuring charming bee-themed decor and gentle music. Plenty of seating and special touches like color-changing spoons create a welcoming space for families.

Milkshakes come with either 4 or 6 scoops of ice cream plus half and half. They taste rich and serve as a special treat.

Black raspberry cheesecake offers a velvety and delicious dessert option. It suits an after lunch treat with a great experience.

People are saying

"The homemade ice cream here is incredible and tasty."

"They had so many great dairy-free options!"

"The ice cream flavors here are unbelievable and unique."

Good to know

1

They accept only card payments; cash is not accepted.

2

All ice cream is homemade and made in-house.

3

Expect unique flavors not found at typical ice cream shops.

05
The Spin Coffee & Vinyl image 1

Space blends vinyl records, cereal bar, and board games with indoor and outdoor seating. Atmosphere stays chill and cozy with a nostalgic vibe from vintage decor and music. Visitors find it easy to relax, study, or browse unique records in a spacious, inviting setting.

Homemade milkshakes include flavors like cookies and cream that taste rich and creamy. Staff sometimes offer a free milkshake, adding to the friendly vibe.

Mexican Chocolate Latte and hot Marocchino offer rich, flavorful options for couples. The spot has good vibes that create a cozy atmosphere for dates.

People are saying

"The coffee here has awesome vibes."

"It's a chill, cozy spot with a great vibe for date spots."

"I had the cookies and cream milkshake, and it was heavenly."

Good to know

1

The store has a cool selection of vinyl records.

2

There is plenty of parking available.

3

Arriving at 10 am is a good time to visit as it's not busy.

06
The Burger Factory image 1
Hamburger restaurant

Counter-style ordering with all seating in booths creates a laid-back diner feel enhanced by classic 50s and 60s music. The interior is clean and stark, with spacious tables and no-frills design. The atmosphere stays relaxed and spotless, making it distinct from typical burger joints.

Milkshakes come out super fresh and pair well with cheeseburgers. They have a classic diner style that stands out.

Couples enjoy trying new burger spots together here. The chocolate shake stands out as a popular choice for sharing.

People are saying

"I found the burgers here to be simple and delicious."

"The burgers here are fantastic, possibly the best ever."

"I enjoyed the cheeseburgers and milkshakes here."

Good to know

1

The single burger costs $4.99, and the version with cheese is $5.99.

2

Everything is ordered a la carte, and a meal for two costs around $35.

3

The restaurant is open late, which is convenient for late-night diners.

07
Maui's on Main image 1
Restaurant

Small restaurant with island aesthetic and outdoor patio creates a welcoming, friendly atmosphere that feels like a Hawaiian vacation. Live Hawaiian music and good tunes add to the pleasant vibe. Seating includes indoor tables and picnic tables with fans and umbrellas for comfort.

Ube milkshake stands out with a perfect rating and creamy texture made from real ice cream. Vanilla milkshake also tastes great, and staff sometimes offer milkshakes to smooth over delays.

Hawaiian Fried Chicken and Garlic Shrimp come cooked just right with a nice taste. The food matches authentic Hawaiian flavors, and the Ube Milkshake offers a unique sweet treat.

People are saying

"These burgers are onolicious and broke my mouth with flavor."

"The food at these Date Spots is delicious, especially the garlic shrimp."

"You have to try their ube milkshake; it's a perfect 10/10."

Good to know

1

Poke is served only on Saturdays.

2

Parking is available in a small, cramped lot with poor paving.

3

They provide a military discount.

08
Chester's Hamburgers image 1
Hamburger restaurant

Rustic old-style burger joint with classic neon signs and a southern vibe sets a laid-back, friendly atmosphere. Oldies music plays softly alongside sports on TV, creating a lively but easygoing environment. Large, fresh burgers and best onion rings attract crowds, especially after local games.

Milkshakes use real ice cream and fruit for a rich taste. The chocolate flavor stands out as a popular choice. They pair well with burgers and onion rings.

Burger options include a bacon burger and a chili burger with crispy bacon. Fresh ingredients appear but some find them lacking in flavor. Couples often choose this spot for date nights.

People are saying

"You have to try the onion rings; they're so crispy."

"I thought the milkshake was the best thing here."

"The burgers here are big, greasy, and extra cheesy."

Good to know

1

Expect a wait time of 20-30 minutes during peak dinner hours.

2

They only accept cash payments of $20 bills and under.

3

A 25-cent charge applies for each paper bag used for takeout.

09
Chris Madrid's image 1
Hamburger restaurant

Hamburger restaurant offers large indoor and outdoor seating with live music and a salsa bar on the patio. Atmosphere feels relaxed and family-friendly with a funky local vibe. Popular for best burgers and icy cold beer alongside tasty margaritas and micheladas.

Milkshakes come thick and delicious, with a caramel option available. People often order multiple milkshakes to go, showing they are a popular choice.

Burger dates happen often here with a casual vibe. Staff and cooks show friendly service even if the cashier can be less welcoming.

People are saying

"I thought their burgers were the best I ever had."

"You have to try the juicy, delicious burgers here for Date Spots."

"I enjoyed my thick and delicious milkshake."

Good to know

1

Happy hour runs all day on Mondays, starting at 3 pm.

2

Live music occurs every Thursday and Saturday from 6-9 pm.

3

The restaurant has a party room available for events.

10
Mr. Teriyaki image 1
Restaurant

Spacious restaurant with Asian-themed decor and soft rock music creates a relaxed, cozy atmosphere. The environment stays clean and inviting, with plenty of tables but sometimes feels crowded and warm. Condiments and a wash sink near the dish pickup add convenience to the dining experience.

Offers taro milkshakes alongside various flavored Buba Teas and smoothies. Milkshakes have a tasty, sweet flavor profile with options like passion fruit and taro.

Combination fried rice features proteins seared to perfection with strong flavor. Bento boxes offer a variety of items that appeal to couples looking for a shared meal experience.

People are saying

"The Japanese food here is delicious and always tastes fresh."

"The teriyaki chicken here is seasoned well and melts in your mouth."

"I found the milkshake here to be delicious."

Good to know

1

The new location has tight parking, so arrive early.

2

Expect a long line to order during peak hours.

3

Portions are large and great for sharing.

11
Dave's Hot Chicken image 1
Chicken restaurant

Chicken restaurant offers vibrant, trendy atmosphere with interesting art murals and natural lighting. Space feels small and crowded with tight seating and a narrow line lane. Outdoor seating is available alongside indoor dining.

Milkshakes come in fruity pebble and vanilla flavors. They serve them cold to help cool down after spicy food. The milkshakes taste very good and pair well with the menu.

Large #2 sliders and shared fries make for a casual, easy meal. Friendly service adds to a relaxed vibe on dates.

People are saying

"These sliders are amazing, with tender, juicy chicken."

"The hot chicken here is actually hot, a rare treat for Date Spots."

"I grabbed one of their delicious milkshakes to cool down."

Good to know

1

Reservations are not accepted; expect long wait times during peak hours.

2

The restaurant has limited seating, especially during dinner rush.

3

A waiver is required for the Reaper chicken due to its extreme spiciness.

12
410 Diner image 1
American restaurant

Diner offers an authentic 1950s retro setting with jukeboxes, classic booths, and Elvis memorabilia creating a nostalgic atmosphere. Music plays at a comfortable volume, supporting a cozy, fun vibe. The space feels like stepping back in time with charming decor and a clean, inviting layout.

Classic milkshakes come in retro style cups with whipped cream on top. The strawberry milkshake tastes like real strawberry, which is rare. Cups are only half full despite the whipped cream.

Cute ambiance creates a quiet setting ideal for early date nights. Staff show personalized attention, remembering guests across sections, while dishes like the chicken fried steak stand out.

People are saying

"The diner has a great retro atmosphere and friendly staff."

"The burgers here are huge and delicious, perfect for sharing."

"The milkshakes here taste like real strawberry."

Good to know

1

On Tuesdays, 410 Diner offers $2 off.

2

Food prices range from $13 to $20 for a full meal.

3

Parking can be tight during lunchtime.

13
Savvy Sliders image 1
Fast food restaurant

Fast food restaurant offers a welcoming atmosphere with a clean, nicely decorated interior and a relaxing outdoor patio featuring large shade umbrellas. The vibe stays chill and inviting, with pop music adding energy. It attracts people looking for a comfortable spot to eat, relax, or study.

Milkshakes come in cookie and cream and Reese's flavors that taste very good. They pair well with slider burgers and have a super delicious quality.

Cozy seating invites couples to relax and enjoy food together. The menu features spicy fish sliders and meaty chicken tenders that keep people coming back for more.

People are saying

"These sliders are packed with flavor and delicious."

"These sliders are delicious, perfect for Date Spots."

"I enjoyed the slider burgers and milkshakes."

Good to know

1

The drive-thru is open 24 hours for late-night cravings.

2

Expect long wait times during busy hours, especially at lunch.

3

The restaurant has cleanliness issues, with dirty tables and floors.

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San Antonio, Texas

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