Ask Boobs Radley: Can I Date An Older, Richer Woman?

Everyone on Twitter considers themselves an expert of one type or another. We figured a woman who grew up with the nickname @BoobsRadley must have plenty of experience discussing issues of love and sex. (Plus, the Huffington Post called her one of the funniest women on Twitter.) Read on to find out how to send your questions to her.

Q: I’m 22 and into a woman who is almost 10 years older than me. We have great chemistry so I’m not too worried about whether she’ll say yes to a date, but I also don’t really know how to tell her that I’m very, very broke (student loans, entry-level job, city apartment). I know she’s very successful and goes out to nice places, which I can’t even afford to go halfway on. Is this doomed from the start?

Uh, does she know you’re 22? Unless you’re one of those super rich kids with an emir dad in Dubai who crashes yachts for fun and lights his Cohibas on piles of burning cashmere coats, I think she knows you’re broke. Everybody is broke at 22! Did you like, weirdly give her the impression that you’re an heir? Were you featured in one of those magazine articles about young tech titans that makes me drink because I’ve disappointed my parents so badly? She knows. So the best thing you can do is come up with cheap and inventive dates and save your pennies in case she wants to go to some fancy-older-accomplished-lady place. And in that case, she’ll probably want to enjoy the fact that she’s a successful woman who’s boning down with a 22-year-old by picking up the tab. A lot of women you date are going to make more money than you. So we can do what you guys have done for years now–either split the check or guilt you into going down on us in a banquette because you HAD to order the crab legs.

Q: When my girlfriend and I were playing the “which celebrity would you..?” game, I mentioned that “iCarly” was in my top five. She’s 18, so I don’t get what the big deal is, but my girlfriend is freaked out because she plays a kid on TV. What’s the big deal?

Oh, you mean the 10-year-old? The 10-year-old child from “School of Rock”? The one from children’s television? Yeah, no idea why that would be weird. OK, in all seriousness, this talk is always a dangerous one and not one that I advise having if you or your significant other are the types of people to obsess about little things. Like, if my boyfriend said that he’d like to have sex with somebody like Laura Dern, who is basically my physical inverse, or I don’t know, Zach Galifianakis, who looks enough like me but would be troubling for different reasons. As Woody Allen can attest, the crotch wants what it wants, but sometimes it’s not always best to share our wackiest, creepiest, borderline white-van fantasies if we’re going to creep out our partner. I’m all for full disclosure when it comes to most fantasies and fetishes. But man, there are some things that should be kept to yourself and buried down deep in the dustiest most shameful vault of your spank bank. I mean, come on dude. It’s not like you have a perfectly normal foot or choking thing.

Q: I’m in college, and I just found out that a girl I’ve started seeing plagiarized a paper. She’s not getting kicked out, thankfully, but I feel really weird and suspicious. If somebody is dishonest in school, does it mean she’ll eventually lie to me?

I’m going to be honest: My initial reaction here was YIKES. Whenever I hear about somebody committing some kind of crime, I always try to think of mitigating factors. Like, if a guy steals a loaf of bread because he’s starving. That’s sort of justified because maybe a French cop will obsessively chase after him and they’ll both sing about it and it’ll make a pretty great musical. Or something. But plagiarizing sucks because it’s like combination cheating and stealing, with a sprinkling of laziness. Sure, it’s a victimless crime if nobody gets caught, and it doesn’t necessarily mean that she’s going to CTRL+C large portions of other people’s penises. But as a reflection of somebody’s personality, it’s pretty low and sneaky. Unless she did it totally unwittingly, like the Dane Cook cribbed large pieces of somebody’s dissertation on Louis C.K.

Q: My girlfriend’s best friend is a gay guy. I have absolutely no doubt that he is into men, but he constantly touches her in ways that I would consider inappropriate for anyone, gay or straight. He sleeps in her bed, “honks” her boobs and kisses her on the mouth when he’s drunk. She doesn’t seem to mind, and says he’s gay as gay can be, but it makes me uncomfortable and weirdly jealous.

Touching somebody’s boobs or smooching a lady against her will is not OK. I mean, according to basic decorum and probably most of the lawsuits involving Andy Dick. I don’t care if you’re gay or straight or if you’re one of those super smart guinea pigs from “G-Force,” which I assume are held to a human standard of conduct because of their extreme intelligence. The operative words are against her will; it’s possible that your girlfriend enjoys kissing her gay friend, you know, like that one lesbian from “The Real World” who was only into dudes (what a confusing season that was, for Genesis and for all of us). Brass tacks: if you don’t like it, tell your girlfriend it makes you uncomfortable. I don’t think it’s unreasonable to ask somebody with whom you’re ostensibly in a monogamous relationship with not to–sighing heavily at having to type this, here–get “honked” by other people. If she says no, then I suspect something is amiss here. Plus, who touches boobs in public? Just because it’s weird, sexually confused impropriety doesn’t make it any less impolite.

Q: I’m a well-dressed dude who likes nice things. Vintage satchels, Hermes, good shoes, that whole deal. I’m seeing a really brilliant girl who I like a lot, but she makes a point of how much she doesn’t “go for” fashion. I wish this didn’t bother me, but it does. I feel like somebody who can’t appreciate style is ultimately going to be tone-deaf to a lot of my interests. Am I being shallow?

No! You’re being sensible. Not into fashion? She’s obviously a huge gay lesbian monster. RUN! I don’t know, man. I’ve dated guys who have huge gauges or statement mustaches or who wear those cammo cargo shorts with man sandals. Haven’t you ever seen a movie? Sometimes well-dressed people are sociopaths or murderers, like Patrick Bateman or “The Devil Wears Prada.” Lots of noted aesthetes and thinkers were notoriously poor dressers, like that redheaded chef who wears Crocs. If you guys really don’t mesh, interest-wise, that’s one thing, but being a judgmental b-hole because someone otherwise great is not into fashion is not an attractive quality in a dude, like most qualities that are best left to Tyra. Plus, any girl that’s going to be seen in public with you and your “vintage satchel” should get some kind of humanitarian award.

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