May 29, 2009
Libby, 21, Ithaca College
I've just moved back into my parents' house. How do I bring a date home without awkwardness?
Quietly bring them home after two a.m.. Otherwise, you're screwed (and not in the good way). If your parents still want to know every detail of your life, it's impossible.
I'm horrible at noticing red flags when I start seeing someone. What's the number one warning sign that I shouldn't keep pursuing a new guy?
This is definitely my problem too. Other than the obvious signs like STDs, if he seems to have too much time available for you and he's willing to ditch his friends for you, he's a creeper who's looking for a dependent relationship. It might be flattering now, but it won't be when he's wants you by his side alllll the time.
I'm really into having sex in the morning, but my boyfriend isn't exactly an early riser. What can I do to help him get started?
Are you sure he's a guy? Strip naked, whisper in his ear that you want to have sex, and reach for his junk. He'll be up.
I teach high school, and one of my former students — who is in his mid-twenties now — asked me out to dinner. I want to accept, but how can I avoid awkwardness over how we met?
If you don't want any awkwardness with former students, perhaps you should stop talking to your former students. Just a thought. Otherwise, laughs are the best weapon against awkwardness. So maybe laugh about old school stuff or something else.
My boyfriend and I want to try getting busy somewhere public. What precautions should we take to ensure a speedy getaway, should anyone spot us?
Know your exits. Do a test run. And wear a skirt.
Becky, 21, Bard College
I've just moved back into my parents' house. How do I bring a date home without elaborate schemes or incredibly awkward encounters?
Does your date have his own place? He'd better, because hushed sex in your parents' basement is so very 2003. I'd wait to bring him home until it's one you can call your own.
At a party, I drunkenly hooked up with a friend-of-a-friend but don't remember it. I'll probably see him again, so what's the best way to diffuse the tension when I do?
I never forget when I hook up with someone at a party, no matter how hammered I am. Blaming it on the alcohol is just cowardly. So just act normal and be cool, but don't pretend like nothing happened. That's just a slap in the face no one needs.
I'm really into having sex in the morning, but my boyfriend isn't exactly an early riser. What can I do to help him get started?
Well, I hate morning sex most of the time, so what my boyfriend does is poke me in the back with his hard-on until I grudgingly turn around. Works for him, it can work for you! Just cajole him with caresses. Most guys get morning wood anyway, so capitalize on it and head on down there with a mission to please.
I teach high school, and one of my former students — who's in his mid-twenties now — asked me out to dinner. I want to accept, but will there always be awkwardness because of how we met? How can I avoid that?
Slow down, Mary Kay Letourneau. You might want to reconsider taking the offer. Just because it's legal doesn't make it un-creepy.
My girlfriend asked me to be rougher in bed — tug her hair, pin her down — but I worry about being disrespectful somehow. How can I get over this and give her what she asked for?
Dude, do it! It's okay to have completely different rules inside and outside of the bedroom. You just have to get familiar with the girl's boundaries.
My boyfriend and I want to try getting busy somewhere public. What precautions should we take to ensure a speedy getaway, should anyone spot us?
If you're worried about being spotted you're missing the point. Be spontaneous and don't worry about repercussions. But as long as you're asking: wear a skirt or some shorts — much easier to pull on and off than pants. And don't take off too much clothing. Do what you need to do while keeping as many garments intact as possible.
Andrew, 22, Skidmore College
I haven't found a job yet, but I don't want to just tell my dates that I'm unemployed. Is there a way to make job-hunting sound sexy?
Just say that you have plans to travel a bit before you get a job. It's a great conversation topic and it makes you seem a bit more free-spirited and cultured.
What's the best place to take a recent college graduate on a date?
A job fair.
I'm a guy who just graduated, and now I don't know what age group I should be dating in. How do I date older women without seeming immature, or college girls without seeming pervy?
Fudging your age isn't just for the ladies anymore. A little white lie can make you seem just as mature as you need to be.
I'm going to a dinner party with my new boyfriend, and my ex will be there. How can I warn my current guy without poisoning the evening?
Tell him all the bad things about the ex. It'll give your new boyfriend a smug feeling of superiority, and he might even be nice to the ex out of pity.
I'm really into having sex in the morning, but my boyfriend isn't exactly an early riser. What can I do to help him get started?
Get started without him. It's a very pleasant way to wake-up.
My girlfriend asked me to be rougher in bed — tug her hair, pinning her down — but in the moment I worry that I'm being disrespectful somehow. How can I get over this and give her what she asked for?
Ask her to demonstrate what she wants on you. You won't feel disrespectful if you are just reciprocating.
Callie, 22, Boston College
I haven't found a job yet, but I don't want to just tell my dates that I'm unemployed. Is there a way to make job-hunting sound sexy?
Do temp work! Since graduating, I've helped my ninety-year-old male boss urinate, managed plumbing disasters at a condo complex, and calmed irate tax clients. And that's not even the half of it. Bottom line, my stories are a hell of a lot more entertaining than your 401k. There is never a lull in conversation and all my dates want to be me and bang me at the same time.
What's the best place to take a recent college graduate on a date?
How about yard-sale hopping? You'll get plenty of time to converse, and even if your date is an intolerable bore, you'll score some cheap digs for your barren apartment.
I'm working a night job right now, which makes it hard to date. What's the best way to take someone out in the daytime but still keep it romantic?
Go for a long hike together on a sweltering summer afternoon — it's free, or very cheap, and the two of you will be alone in the woods, sweating and panting your butts off together. What could be sexier?
I've been flirting with a neighbor whose window faces mine, but I haven't seen her outside yet. How can I move things forward without seeming like a stalker?
Make a sign that says "Can we take this outside?" in big letters, and hold it up to the window during one of your neighborly interactions. You'll get a really hot date or a restraining order. Don't say I didn't warn you.
I'm really into having sex in the morning, but my boyfriend isn't exactly an early riser. What can I do to help him get started?
If you really want to wake a zombie from the dead, you're going to have to work for it. This is your show and you need to keep him captivated and entertained. Start by giving him the best head he's ever received. He'll wake up happy and ready to go!
My girlfriend asked me to be rougher in bed — tug her hair, pin her down — but I worry about being disrespectful somehow. How can I get over this and give her what she asked for?
If you want to keep her around, grow a pair and give the girl what she wants! If you get too rough, she'll let you know. I promise. Loosen up and have some fun — next week you'll be thanking both of us.
Questions by Jim Ryan. Dating Advice From... appears on Fridays.