7. Looking (and Being) Generous When You Have Less Money Than Your Friends

Do you have friends who always, always have spending money? Friends whose parents give them credit cards to just use? Friends who constantly and casually pay for things like meals and snacks and movie tickets, sometimes taking care of you in the process?

Hiya. This was—and is—me. In the past, in the present, and probably for all time. I grew up with less money than any of my friends. We weren’t flat-out broke, but I most certainly did not have casual spending money, and there was no way I could wander into a store and just purchase something like a cool T-shirt. All purchases had to be carefully plotted in advance and saved and schemed for. A lot of my friends, having always had access to plenty of money, simply did not understand that if I went to the movie, I could not go for pizza, and that was that.

It’s still like that today. I have friends who make six figures and are always ready to go out for fancy drinks, friends who casually drop $250 at Whole Foods in 20 minutes, friends who want to go to that new award-winning restaurant where entrees start at $35 because it just opened and they’re hungry and it’s Tuesday. If I say, “Umm, could we maybe go somewhere…less spendy?” they’re all over it. “Oh, I’ve got you,” they say, waving their hands in the air. “Baby, don’t worry, I’ll get you. Just come.”

That’s nice as hell, but a lot of times, it makes me feel like an asshole. I don’t want someone to “take care of me.” I don’t want to always be on the favor-receiving end. It skews the balance of our relationship in a way that makes me feel like I owe the person covering me something, but I can’t afford to ever make good on this debt or to right the balance between us. I feel this even though I know my friends don’t think I owe them anything, and that they’re offering to pay out of total friendliness and love. It’s just that it doesn’t always feel so great to me, in my head. Know what I mean?

If you have wealthier friends who are constantly doing you monetary favors, I have a way to feel better, seem generous, and balance the friendship scales: Spring for the small stuff.

When the opportunity arises, use your limited funds to pay for little things, without announcing it or making it a thing in any way. If your friend with a great allowance constantly buys your lunch, buy her coffees when y’all go out. If someone insists on getting your movie ticket, hop quick like a bunny and pay for the popcorn. Even tiny things, like buying two orange juices from the vending machine and silently handing one to your friend, make a huge difference.

These are small things you can do to show that someone’s generosity does not go unappreciated, and believe me, your friends will notice. You are showing that, while you may have less $$$, you are willing to share what you have, and that makes for a balanced and mutually generous friendship.

And if you don’t have any money to spring for the small stuff? It’s really OK. Don’t be afraid to say sometimes, “Hey, I’d love to do that, but I can’t afford it, and I don’t want you paying for me all the time,” and then stick to your guns. On the occasions when you do accept a favor, thank the friend who spotted you and try to think of a way to help them. Maybe you’re really, really good at algebra, which that person sucks at. Study with them. Maybe you’re just an awesome listener who gives amazing hugs. You can still pay them back in your own way, free of charge.

8. Asking a Stranger Out

You notice a cute new person working behind the counter at a your regular coffee shop. Or you see a cool someone at a library/concert/reading/museum/restaurant. They’re in your line of vision, and suddenly, BAM! All of your radiant energy is directed like a laser beam on this person who you don’t actually know. OH MY LORD, NOW YOU KNOW WHAT PERFECTION LOOKS LIKE. You want to talk to this person; you are filled with a desire to know them. But they might leave at any moment! And you may never see them again! This is your one chance in life to ask this person out. Do it. DOOOOOO IT.

“But Krista!” (That’s you.) “I don’t know anything about them! What if they’ve got a girlfriend or boyfriend already? What if they’re gay? What if they’re not gay? What if they’re asexual? What if they just get hit on every day (OBVIOUSLY THEY DO, LOOK AT THEM!!!) and are totally sick of it and want nothing more than to be left in peace?”

Guess what? I DON’T CARE. These are all useless details, clouding your shining brilliant nerve. Get ready to become instantly bolder, because I’m going to teach you how to ask a stranger out in the quickest, politest way possible, with way fewer scary rejection possibilities than usual. You won’t have to have any prior knowledge of the object of your sudden affection’s situation—and the ball will stay COMPLETELY in their no-pressure court.

Here’s what you do:

1. Scan your crush-target for headphones/work/body language that says DO NOT APPROACH. Don’t ever bother someone who’s wearing headphones (aka the international sign for “leave me alone”), who’s hunched over a book or a laptop, or who looks super-busy, like a café worker who’s got a big line. Would you like that? ’Course not. Respect people’s body language, space, and time.

2. If you’ve determined that now is possibly an OK time, gather all your stuff. Get totally ready to go. Use the restroom, put your coat on, everything. Asking someone out will be the last thing you do before leaving this place.

3. Find a slip of paper and a pen. Write down your name, your phone number or email address, and a short description of who you are and what you look like. Example: “Krista – the blond girl with cat-eye glasses who asked you out at Swim Café. You can reach me at [email protected]” Be brief! What you are about to do will be memorable.

4. Take a deep breath and approach this dreamboat.

5. BE BRAVE! Smile and say, “Hi, my name’s [your name here]. I don’t know what your situation is, but I think you’re really cute. I’d love to hang out sometime if you want. Here’s my info.”

6. Hand them the pre-prepared slip of paper with your information on it. Smile again. You are a brave and confident person who has no fear!

7. VANISH. Seriously. Vanishing is the secret to asking a stranger out without too much awkwardness. If they try to talk to you, cheerfully say, “Sorry—I have to go!” One more smile, then get the hell out of there. This makes it so there is absolutely NO PRESSURE on your new crush to respond to you. They have a way to contact you. If they’re interested, they’ll get in touch. If they aren’t, who cares? No harm done/no feelings invested.

Guys, this really works. It does! I’ve been doing it for years, and I’ve also taught this to every shy friend I’ve ever had, with excellent and sometimes even astonishing results.

Go get ’em, killer. ♦