Dear Ty

Dear Di,
Things always start off alright for me with the ladies, but what seems to be the beginning of a blossoming relationship always ends with the “nice guys finish last” aphorism for me. Do you have any advice for us “nice guys” who keep getting sidelined by the likes of “You’re a really great guy but…” and/or “I wish I could find a guy like you…” or any of the other lines that get us sent to and stuck in the friend zone?

—Nice Guy Stuck in Last Place

Dear NGSLP,
I’m not a fan of the nice guy stereotype. Just because you’re nice, doesn’t mean a woman automatically has to be in a relationship or have sex with you. There’s been huge backlash in the feminist community against “nice-guy syndrome” because niceness should be a human quality, not one you employ because you think it entitles you to automatically get lucky. I suggest you look said syndrome up. Besides, I just haven’t found the stereotype to be true. Sure, a lot of douchey dudes end up in long-term relationships—but so do a lot of really sweet, genuine, kind men. You know who has a hard time getting girls? Shy guys, guys with little to no self-confidence, guys who don’t make it clear that they’re interested in girls, and boring guys.
Is it possible that you fit into one of those categories, but instead of addressing what’s keeping you from sealing the deal, you’re blaming your courting woes on being nice? If you’re shy or don’t have much self-confidence, the vibe you’re giving off isn’t one that tons of women will be attracted to. Self-assurance is sexy. If the chick you’re trying to get doesn’t know you want her—whether that’s because you’re afraid to get hurt or because you think you’re being “nice” by approaching women in a friendly rather than romantic fashion—of course you’re going to be relegated to the friend zone.
I’m not telling you to be predatory or to go around using lines on ladies to let ‘em know you want to start something intense, but you can be direct while still being respectful. Take the next step and actually ask a girl out on a date. Be clear that it’s a date you are looking for, and recognize that not every girl you talk to is going to take you up on that offer. That has nothing to do with you being nice or not; it has to do with whether you have similar interests, whether or not she’s attracted to you, and whether or not she’s available.
The other possibility for why you’re facing rejection time and time again? You’re boring. I’m not saying that’s the case, but my advice is this: cultivate your interests, read more books, join a club or sports team, visit new parts of Ottawa, grow a garden, take up an instrument. When you’re busy being an interesting and fun human being, you’ll meet more people, including someone you might want to date and who might want to date you back.
Good luck in the race, friend—I hope you finish first one of these days!

Love,
Di

Dear Di,
I’m a guy who can’t come from oral sex. I’m normal when it comes to regular sex, but blow jobs just haven’t done it for me yet. My girlfriend is getting upset—she says her last boyfriend came fast during BJs. She’s losing self-confidence, Di. I want to be able to come when I’m in her mouth, but it’s just not the same as thrusting into a vagina. What can I do?

—Fully Loaded but Malfunctioning

Dear FLM,
Not being able to come from oral sex is totally normal. Some guys and gals have written to me saying they can only successfully reach their peaks when they have sex in very specific positions or certain environments. In your case, it may be a case of BJs just not pushing the right buttons, or maybe you need the actual job done a little differently.
Your first step is to assure your girlfriend she has nothing to be self-conscious about. If she starts to feel like she can’t get you off because there’s something wrong with her, she won’t be able to perform—that’ll make the situation worse for both of you, that’s a risky downward spiral.
Another thought: this might be a problem with your big head, not your little head. If you’re uptight, nervous, or thinking too much during a blow job, you’re almost definitely not going to finish. In that state of mind, you won’t get off regardless of how tight, wet, or soft the flesh surrounding your cock is.
The alternate explanation is just as simple: a mouth feels different than a vagina does, and sometimes one or the other just doesn’t do it for everyone. Enjoy what you’ve already got going on in the bedroom, and the rest may come (pardon the pun) with time.
Something you should try if you’re both down: have vaginal sex, but finish in her mouth. That’ll give you the end result you want, and might calm your nerves or help you associate her lips with your orgasmic bliss. Try other techniques too: have her blow you and end with a handy, and see if that makes any difference. Have fun with no pressure on either of you, and the cum is sure to follow. Also, I’m not sure what your routine is like, but if you’re doing the arm wrestle with your one-eyed vessel on your own a little too frequently, that could be a factor. Cut down on masturbating for a while, and see if that helps any.
Aside from that, I can suggest you get your girl to take it like a Louisville Slugger: both hands at the ready, giving it all she’s got. It really could just be a question of your rifle needing a little more diligent cleaning, and it could just take longer. You both need to be patient and enjoy it; don’t put too much pressure on yourselves. Oh, and be sure that while you two are working on blowing your cannon, that you spend a decent amount of time muff-diving as well.

Love,
Di