NON RED-FLAGS
Need for discretion. If a man doesn't tell you much about himself, his job, or his life, is using a Google Voice number or a fake email, is going by a fake name, it does not matter at all. But, sometimes a man's "need for discretion" makes it impossible to find out anything from him. In that case, I say "While I respect your need for discretion, it does not trump my need for safety and I would not feel comfortable meeting you for dinner without...(at least a skype date)(as many photos as I've sent you)(information about XYZ)(etc.)." If he refuses to accommodate, he's blatantly disrespectful of your safety concerns and he's not worth your time.
RED-FLAGS
Asks for sexy photos. You really need to make sure your profile photos serve their purpose and depict what you look like from head to toe. If you only include iPhoto face shots, that's dandy but you need a full body shot of you in a cute outfit and I also always include a bikini shot. Nothing raunchy, just a fun day at the beach. If they're asking for sexy photos and you already have full body shots on your profile, then kindly end it because they're 12 year old horn dogs stuck in 45 year old bodies. But if your photos suck and they just want to confirm that you're not Shrek, then you need to amp up your profile and oblige.
Asks your favorite position, kinkiest moment, sex history, what you're into etc. There's no space for immature, tacky, desperate rapid fire sex questions in the sugar bowl. At its core, sugaring is about companionship, chemistry, and fun times. If he needs a rap sheet of what you will and will not do in the bed room, then he should call up a pimp and ask for a very specific hooker. Even if you tell him this and he apologizes and stops, you still know that that's his main incentive for joining this site so he's probably looking for pay for play but has too much pride to admit to wanting a prostitute. If you're fine with 4 hours a month with this man for however much you agree on, then boom! You just landed on easy money. But if you're looking strictly for a sugar arrangement with outings, dinners, etc. then you need to move on. But be mindful that a lot of these men might be into BDSM, so if they ask specifically if you have interest in that then that's not necessarily a red flag so much as them not wanting to waste either of your time. If you do say yes, however, and he presses you with sex questions, he's equally guilty of the above offense.
Sleezy username/bad grammar. If "Hotsex69" messages you, you already know what he's there for. He's not a sugar daddy. He's blatantly looking for pay for play.
Takes offense to your precautions. A lot of men will quickly realize that you both have iPhones and that your messages aren't coming up blue. If he questions it, let him know straight up, "I'm using an app called Google Voice so that I don't have to share my real phone number with strangers. Once I'm comfortable enough with you, I will give you my real number and you can reach me there." 99% of guys completely get it and think "Damn, I wish I'd thought of that. She's smart and safe and not full of shit! I can tell a lot of guys have wasted her time and I don't want to be one, so I better step it up if I ever want the honor of using iMessage with this hottie!" The other 1% will cry like little bitches and be like "We've hit it off thus far! Don't you trust me?!?" If he honestly thinks trust can be fostered after a few email messages, he'll be equally pissy when you don't have sex on the first date or when you reject his marriage proposal on the second date.
Insists on meeting for just drinks. 10:00pm drinks at the hotel bar so you can get drunk and then go upstairs? Um no. In a fun way, tell him you'd rather meet for dinner at this great restaurant you're dying to try yada yada. I had this one guy come back at me with "How about we start with drinks and if we hit it off, then we can get dinner?" I literally see no incentive to that besides wanting to roofie me. If you're that awkward and can't be around a younger, more attractive woman without drinking then let's drink at dinner. Have 10 glasses of wine with your food. I don't care. But if I'm getting dolled up, I'm eating food. You are not skimping out on buying me dinner and you are not roofie-ing me and you are not getting me drunk so you can drag me back to your lair. I do too much damn cardio to drink my calories. Buy me dinner, you fuck.
