Should You Break Up with a 'Casual Hookup' in Person?

We’ve been hooking 

up for about a month. I’m over it. Do I need to break it off in person?  
JUSTIN, TORONTO, ON

These days, no. If it’s truly been a casual hookup—and if she definitely viewed it that way—there’s no need to risk embarrassing her. If you didn’t see each other all that often and things were mostly physical from the get-go, then just move on.

However, you’ll have to remove all sources of temptation so you don’t go crawling back to her when you’re feeling randy: Delete her from your phone, hide her on Facebook, and—most important—do not answer when the inevitable booty call comes. She’ll get the message.

Women say they love tattoos, but where do they draw the line between stupid and sexy?
MIKE, LAS VEGAS, NV

A tattoo is stupid when it has no meaning or a bad story attached. So find a good artist, and go sober. If it has words, check the spelling. If it has Chinese characters, make sure they say what you think they say.

Reconsider barbed wire, your girlfriend’s name, superheroes, dragons, and cartoons. And make the story behind it a good one, because she’s going to ask. Bonus points if it doesn’t involve the words “this one night” or “Tijuana.”

(She may like the way they look, but tattoos are a risky choice for some careers. Here's how Tattoos Might Be Costing You a Job.)

How can I break it to her that I hate the infantile pet name she gave me? 
PAUL, DES MOINES, IA

It’s easy, Pookie. Just say these magic words: "My ex used to call me that.” You’ll never hear those cutesy syllables strung together in your presence again.

But if you’re less than eager to conjure up ghosts of girlfriends past, try this instead: Tell her how sexy you think it is when she calls you “Paul” in bed. Once she knows it’s associated with a turn-on, she’ll be more likely to use a name fit for a man, not a boy.

My girlfriend just lost her job, and now she’s worried about rent. I can float her, but should I?
DONALD, ATLANTIC CITY, NJ

Few things complicate a relationship more quickly than an IOU, so put your wallet away until she tries other options, like her family.

Lend a hand in more meaningful ways: Help her update her résumé, proofread her cover letters, and ask everyone you know about job openings she might qualify for. Because even better than writing a check is finding her a job that’ll let her keep writing her own. 

I screwed up again. What’s the best 
 “I’m sorry” gift?
BARRY, SPRINGFIELD, IL

In situations like this, a woman doesn’t want more stuff. Write her a note instead. By hand, on paper. It’s formal 
and unexpected and shows you’re being thoughtful.

And unlike 
a hasty apology text, 
a note won’t set you up for an autocorrect fail. She wants you to show that you understand exactly how you’ve hurt her feelings. She also needs you to be truly sorry.

A sincere note—one from the heart—will convey that message better than any bouquet ever could. Follow up with a home-cooked meal, and she might just swap dessert for makeup sex.

(For more dating and relationship advice from Ali Fedotowsky, get her take on Oral Sex: Should You Always Return the Favor?)