Here are some ideas to up your date night game.
Weekly Weekday Escapes

Tasty Takeover Tuesdays in the Milk District - Tuesdays from 6:30 PM - 10 PM

Taco Tuesday at Wall St. Plaza - Tuesdays from 2 PM to 2 AM
$3 Tacos, Margaritas, Coronas, Modelo, Dos XX and Tequila Shots

Unwined Wednesdays at Kasa - Wednesday's from 5 PM to 9PM
$15 Ladies $20 Gentleman - unlimited wine, select beer, champagne, house sangria and apps

Tapas Tuesdays at Ceviche Orlando
$4 hot and cold tapas $4 sangria

Wanderlust Wednesday at Ivanhoe Village - Third Wednesday of each month from 10 AM until 9 PM
$25 per person - stroll through Ivanhoe and sample drinks at different establishments
Monthly Weekend Events

Adults-Only Science Night Live
October 7 from 8 PM - 11:30 PM
Orlando Science Center ; 777 E Princeton St, Orlando, FL 32803
$15.95 per person - fun exhibits and programs + drinks
More info here

Get Your Jazz On
October 27 from 6:30 PM - 9:30 PM
The Alfond Inn - 300 E New England Ave, Winter Park, Florida 32789
$65 VIP Seating
$50 General Admission
Unlimited select wine, beer, crafted cocktails, roasted chicken, roasted pig, vegetarian selections, smoking lounge, halloween attire optional, prizes for best costume, complimentary valet parking
More info here
Festivals

Artlando 2017 - September 30 11 AM - 11 PM
Orlando Loch Haven Park - 900 E Princeton St, Orlando FL 32803
Music, dance, visual arts, film and food.
Free admission
More info here

2017 Brunch Festival
September 20 from 12 PM until 4 PM
Orlando Festival Park - 2911 E Robinson St, Orlando, FL 32803
50+ Cocktails & Craft Beers, tons of delicious brunch dishes starting at $4, live music and games & prizes
General Admission (11+): $16.82
Drink Sampling Admission (21+): $37.92
VIP Admission - Early 11 am Entry (21+): $64.29
More info here

Winter Park Wine & Dine Fall Edition
October 18 from 6:30 PM until 9:30 PM
Winter Park Farmers Market - 200 W New England Ave, Winter Park, FL 32789
3 hours unlimited sampling, live music, vip early entry
Early Bird General Admission: $39.00
Early Bird VIP with Early Entry: $75.00
Ten General Admission (Group Rate): $350
More info here

International Food and Drink Festival
September 30 from 11 AM until 2 AM
I-Drive 360 - 8445 International Dr, Orlando, FL 32819
Free admission & free parking
More info here

Orlando Beer Festival
November 11 from 1 PM - 5 PM
Orlando Festival Park - 2911 E Robinson St, Orlando, FL 32803
The 3rd Annual Orlando Beer Festival is one of the largest beer festivals in Orlando, pouring 200+ craft beers from local and regional breweries.
Advance General Admission (21+) 1 PM Entrance: $40.00
Advance VIP (21+) Noon Entrance: $60.00
More info here