Dear Anna,
I just moved to the city and don't know that many people. I slept with a guy recently-he's pretty cute, and funny, but the sex was just OK, and I didn't feel much of a spark. Should I bother sleeping with him again? -Winter Blues
Dear WB,
Eh. I guess it depends on how desperate you are to take a date to the Christkindlmarket. Based on your glowing review, however, I'd say you probably should just be pals (or pals with benefits if you think the sex might improve with increased intimacy and determination). But, if that's not your cup of glogg, then just stick to friendship while you learn the city and meet new people. There's no need for repeat, sub-par screwery simply because you don't know many people yet. Now is the time to cultivate any lingering interests or hobbies you might have put off in the past. Taekwondo? Competitive skeeball? Amateur French macaron baking? Whatever you're into, do it. Staying active will help you beat the winter blues AND meet people AND make baller macarons, which are pleasing to both the palate and the self-esteem. Good luck, WB, and here's wishing you a future filled with enthusiastic lays and pastries.
Dear Anna,
I've been dating a girl who I'm really attracted to for a few weeks, but the sex so far has turned out to be awful. What should I do? Move on? -Wandering Eye
Dear WE,
Huh. Is there a "bad sex" epidemic happening in Chicago this week? ARE YOU THE BOY HALF OF THAT FIRST LETTER? Because if you are, you're basically in the plot of a rom-com at this point and I implore you to slog through this unhappy middle part to get to the spinning-while-kissing-at-the-end part where you overcome very tame obstacles and fall in love at a Cubs game and eat one hot dog between you and lick mustard out of each other's bangs and THE END.
In the very likely case that you're not that person, well, here's some advice that doesn't involve hot dogs. "Awful" is a pretty strong word for an activity that ends in pleasing body spasms. "Awful" sex to me means that somebody passed out while IN COITUS, or joyfully farted throughout the whole thing. Do you really mean awful, or is it just kind of meh?
If it's the former, then please move on. If it's just that she's super quiet or is fairly reserved, she might just need to be drawn out and coddled a bit before she'll come out of her shell. Talk to her. Ask her what YOU can do to make sex more fun for her. Most people just assume we know what the other wants in bed, but that is so rarely the case. The only way sex gets better is to talk about it. When we talk about "good" lovers versus "bad" ones, it's not really about who has mastered the Karezza Method or who can incorporate fruit compote into their blow jobs -- it's about asking questions and paying attention to the answers. Are you a good listener? Are you both receptive to your partner's desires, within reason? Bam! Your sex just got better, no contortion or condiments necessary.
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