Wondering where to take your special someone for Valentine’s Day? Wanting to finally ask that person you’ve had an eye on to be your “valentine?” Or are you in need of someplace fun to go with your long-term beau?  With Valentine’s Day comes pressure to have a perfect, romantic evening.  Hopefully this article will help take some of the stress out of trying to plan the ideal night and give you some advice for different kinds of relationships.  Here are some ideas for every circumstance, including specific local places you can check out:

First Date
Plan something simple and short, yet thoughtful.  This is the “getting to know you” stage.  Don’t plan something that will last all night or that could get awkward, and if all goes well, you can always extend the night.  For this occasion, Candlelight Coffeehouse, Wine Bar & Café is perfect (3011 N St Mary’s, 210-738-0099).  It’s romantic for Valentine’s Day with comfy seating and has a great atmosphere but is still slightly informal.  You order at the bar and the food is brought to your table.  The food is pretty fast, too, incase things aren’t working out as planned.

Second Date
The first date has covered the “getting to know you” base, and now you can get a little more romantic with the traditional dinner and a movie.  Cooking at home may still be too intimate, but a nice dinner out and a movie is the perfect route to take.  …Better yet – at the Alamo Drafthouse (618 NW Loop 410, 210-677-8500) you can accomplish both at one place.  Drafthouse is an ideal place to go for a second date because you already got to know the other person, so not as much chit chat is needed to make the night special.

Blind Date
One must approach a blind date with a certain degree of caution.  Things could get weird if you plan a long outing and things go sour.  The popular Trinity hangout, Bombay Bicycle Club (3506 N. Saint Mary’s, 210-737-2411), is a good place to go for this occasion because it’s most likely familiar, and there are plenty of yummy drinks to down if the date doesn’t turn out so well.  However, if you hit it off, unique seating (like loveseats) is available so you have the option to cuddle up, or you can seek privacy outside.

New Relationship
Congrats! You are now past the “going out” stage and are entering the “official” dating stage.  In a new relationship, you continue to learn more about each other, but you know you are compatible.  You’ve likely experienced the “dinner and a movie” date numerous times, but a romantic evening in will undoubtedly foster an even closer relationship.  Boys, if you cook your girl some food and light some candles, you will capture her heart, leading to a blossoming relationship.  For a new relationship, show each other how you feel with dinner in and drinks.

Long-term Relationship
You know you partner’s preferences and what they like to do by now.  For Valentine’s Day, you know them well enough to try something new and “out of the box,” or you can stick to your favorite romantic night, but something special will keep that spark ignited.  You could go on a romantic walk on the Riverwalk and eat somewhere special.  A place with an amazing view near the Riverwalk is the Chart House Restaurant atop the Tower of the Americas (601 Tower Of Americas Way, 210-223-3101).  It rotates while you dine, so you can see the whole city.  Lastly, a cool idea would be to reserve a carriage ride downtown.  There are several companies that provide this service including Yellow Rose, Lonestar, and Bluebonnet Carriage Company.

Happy Valentine’s Day, and may your Valentine’s dreams come true.