Being underage and entering the dating world comes with its own set of challenges that not many other guides are willing to tackle. Get advice here on what it means to “go out” as a younger guy.


Asking Her Out

Asking her out shouldn’t be nearly as scary as it sounds. Think about how you would suggest your best friend came over to play video games tomorrow after school. When you ask her to hang out you should do it with the same level of nonchalance.

  • Know what you’re asking for. Before you ask her out you must know what you’re asking for (check out suggestions for great dates here). You’ve got to have a plan for what it is you think you two should do together. Think of how annoying it is when you and your buddies can’t decide what to do, “Dude, what do you want to do?” “I don’t know, dude. What do you want to do?” “I don’t know. What do you want to do?” If you let this happen with you and a girl she’s going to think you’re a total bore.
  • Suggest two options. Always suggest two things to do. They should be in the same ballpark. Having two similar options will make it harder for her to shut you down with a cop-out excuse. If you suggest one movie to see she can reject you by saying she’s not interested in that one – and you wouldn’t know if she wasn’t interested in just the movie or you too. Putting two choices on the table makes her reaction more readable.
  • Be flexible to suggestions. Don’t be locked in to the ideas you offer. If she suggests something else and it still involves the two of you spending time together, go for that. Even if it is something you’re not sure you’d be into, give it a try. Her throwing in another option means she’s still down to hang out with you and that’s what you’re asking for anyway.
  • Don’t push it. If she doesn’t seem too interested back off before you seem creepy. If she has shut down your initial suggestions don’t keep throwing in more – you will only make yourself look desperate.
  • Make plans to make plans. If she’s agreed, make plans for when you will contact her to confirm. Don’t worry about the nitty-gritty details when you first ask her. You can figure out when to meet, how to get there, and everything else on the phone later.

Dates To Take

  • Picnic. This is the “trick up your sleeve” of dates. Paying for a meal for two is probably out of your price range right now. But whipping up something easy in your own kitchen and shoving it in a bag is a great way to spend next to nothing and still put together an impressive date. Avoid classic picnic food like potato salad or deviled eggs and go for something light and fun – fruit salad or chocolate-covered strawberries are both great options. All you need is a blanket, a park, and a sunny day (or even warm evening). When is the last time anyone you knew took a picnic? You’ll stand out from the crowd and seem sweet as sugar at the same time.
  • Ice Cream. This one is as classic as they come. You can probably bet your grandparents went out for ice cream and later made your mom and dad. Gross, I know, but use their timeless wisdom. Even the fancier places won’t cost you an arm and a leg as long as you don’t opt for the largest size they offer. Take your time. Don’t shovel the ice cream into your mouth but take time to talk with her. For a romantic cherry on top (pun intended) act really full afterwards and suggest a stroll when you’re finished to “walk it off”. Ta-da! Now you have a romantic addition to an already great date.
  • Ice-Skating / Roller Rink. A word of warning: this date only works if one of you isn’t a complete noob. If you’re both flailing to keep yourselves upright someone is going home with a broken coccyx and a new “worst date of my life” story to tell their friends. The best is when one of you stinks. It’s an excuse to hold hands and help the other along. Or if you’re both rock stars challenge each other to tricks or races. As long as there is a rink around somewhere this kind of date is light-hearted and light on your pocket. Just make sure to have fun with it!
  • School Production or Community Event. School plays are usually pretty cheap if not free. Don’t search for a big group of friends to sit with or you’ll never have a chance to talk to her. Sit towards the back and whisper comments about what’s going on – a funny story your buddy in the show or how well you think someone is performing. Country fairs are similarly accessible and give you lots of opportunities to walk around, grab playful food like cotton candy or silly games like a sack toss (haha! sack). Don’t sweat it if you don’t win her a giant stuffed animal. Just try and find as many opportunities for fun as you can.
  • In-Home Movie. Sure, somebody’s parents are going to demand the door be kept open or pop their head in occasionally. But as long as you two aren’t on top of each other you’ll survive. Watching a movie at home means you get to talk over it whenever you want to and you can dodge all the awful date snacks that cost a fortune and get stuck in your teeth (read: popcorn or Mike ‘n’ Ikes). Sit down next to each other. Gesture with your hands when you talk and find a way to let your hand land on her leg. If she doesn’t cringe or fling it off it’s a sign the date is going great even if you’re just sitting around on a couch. Finding something to eat in the fridge afterward is a great way to extend the date and, if you linger there for a while, sneak a kiss at a less obvious and awkward moment than at the climax of the film. No gun-toting, explosive action flicks. Keep it light and fun or if you’re both adventurous a horror movie that isn’t overly grotesque.

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