1. Do: Assume that your sugar daddy will want to have sex with you. Sex is always on the table when you enter into a relationship, whether you’re dating the “normal” way, or as a sugar baby.
2. Don’t: Feel obligated to have sex. As with any relationship, you should never feel obligated to be intimate with someone unless you want to be. It’s not a sugar baby’s responsibility to guarantee sex whenever she meets up with her sugar daddy, but if you can find a sugar daddy you genuinely connect with, you might very well want to—in which case, everyone wins.
3. Do: Stay open-minded, remembering that you’ve chosen an unconventional lifestyle.
4. Don’t: Send sexy pictures of yourself to any potential sugar daddy you haven’t developed an in-person rapport with. There’s no reason to give anything away for free when establishing an outright transactional relationship.
5. Do: Orchestrate an IRL meet-up with a prospective sugar daddy as soon as possible. Online back-and-forth becomes tedious quickly and any man who’s serious about moving forward will want to meet you sooner rather than later.
6. Don’t: Express any hesitations about what you’re getting into—at least not with your sugar daddy. It’s exhausting to listen to someone whine about whatever internal conflict they’re having, so if you’re at all conflicted, save it for your friends. Better yet, only pursue this type of relationship if you’re 100 percent sure that the lifestyle is for you. Do whatever soul searching you need to before jumping in.
7. Do: Remain as honest with yourself as possible about what you’re getting into. As a sugar baby, you’re seeking to enter into a mutually beneficial, transactional alliance that is most likely temporary.
8. Don’t: Be shy. Your sugar daddy shouldn’t have to work hard to engage you.
9. Do: Be especially direct on the first date about what you expect in terms of an allowance, payment (credit card debt pay off, help with college tuition, pure cash, check, paypal, gifts, etc.), and your availability (where and when you can meet, and for how long).
10. Don’t: Misrepresent your needs or expectations. When negotiating, don’t hold back. And whatever you do, don’t suggest changing the terms of your agreement midway. If you try to negotiate more favorable terms in the midst of dating, you will probably alienate your sugar daddy, who will view your sudden request as overly opportunistic.
11. Do: Ask a lot of questions about what your sugar daddy expects from you in terms of availability, types of dates (casual, fancy, public, private), sexual intimacy, etc. The idea is to be as open as possible, so conceivably both parties should welcome inquiries.
12. Don’t: Waste a sugar daddy’s time. Time is a wealthy, successful man’s most valuable commodity. So don’t beat around the bush or cancel on him or try to change plans or deviate from an agreed upon schedule.
13. Do: Tell your sugar daddy why you need his help. He’s more likely to want to help—and keep helping—if he understands what your long-term career plans and overall objectives are. Also, be sure to remind him just how helpful he’s being along the way by expressing gratitude and providing specific examples about how your life continues to improve thanks to him.
14. Don’t: Be an ongoing sob story. Balance whatever negative things you say with the positive things going on in your life. Your sugar daddy is there to help, but he’s not there to take on your problems. You never want to come off as desperate, even if you sort of are. Sugar daddies want to feel like they’re making a difference in a sugar baby’s life, but they don’t want to feel sorry for you along the way. This is a relationship, not a pity party.
15. Do: Look your absolute best each and every single time you meet your sugar daddy. And be on point, mentally. Your sulky sweatpants self is for nights spent at home alone. Your sharp, witty, beautiful self is the companion your sugar daddy’s paying for. Be authentic—but be the most pleasant, gregarious version of your authentic self.
17. Do: Remember that your sugar daddy can break up with you without warning, just like any other boyfriend. Save as much money as possible, and solidify another source of income so you’re not 100 percent reliant on a single person financially.
18. Don’t forget that you can break things off, too. If at any time you become dissatisfied, call things off and move on. There’s always another rich, wrinkly fish in the sugar daddy sea.
19. Do: Let yourself get close to him. Your sugar daddy should be someone you respect and truly like—someone you genuinely want to spend time with and learn from. It’s only natural for you to become close over time.
20. Don’t: Get too attached. There’s always the possibility that a sugar baby and sugar daddy will fall in love, but long-term attachment isn’t usually the main goal. Sugar dating relationships are generally about what works for both parties in the here and now, but not necessarily down the line.