How Do I Sleep With Multiple Girls in a Friend Group, Plus What’s the Worst Place to Get Hard?

Q: My girlfriend goes to a college in a different city, and her birthday is coming up. Need tips for how to make the day special for her even though I can't be there. Thanks.

A: Well, thoughtfulbreau, my condolences on the geographic spread.

Been there, done that, hated it. Long distance can be a real relationship-killer, so I certainly commend the efforts to keep the love alive. 

Here are some options to maintain that blossoming romance, if only long enough to get you past the Christmas threshold. It's always awkward to break up during the Holidays. 

1. Keep it simple with the romantic one-two punch. Have flowers delivered to her in the morning accompanied by a sweet card. Send her to her favorite coffee shop with bagels and pastries already waiting for her. 

2. Surprise her with a plane ticket. To keep the fire burning, it’s pretty obvious that you need to see each other once in a while. So if you're willing to dish out the dough, buy her a flight to visit you. Print out a copy and send it via snail mail to arrive on or before her birthday and she'll be thrilled.

3. Go for the subscription gift. Wine, beer, or a chocolate of the month is a gift that keeps on giving. And unlike the herpes you passed along to her, it'll be a positive monthly reminder of how much you care about her. However, this option is not for the uncommitted. If you foresee a breakup within the coming year, DO NOT choose this. It is fucking awkward for all involved to send/receive a present on a monthly basis from someone you're no longer dating.

My roommate still receives a box of specialty chocolates each month from her ex of six months, so I would know.  Since I'm a really good friend, I take the awkward burden off her hands. I hope she returns the favor at a different time.

Q: I'm a single guy in my late 20s and I work roughly 80 hours a week, non-negotiable for at least a few more years. In the city where I work, it seems that most people have paired up after college and there are very few singles out there. Plus, many of the girls I meet are younger than me and have a boyfriend. Many have been married for YEARS. I'm flirty with any girl I think is cute with no ill intentions and usually get reciprocation from the girls. I've always seen it is as a dog move to go after another man's girl, but it seems like guys are calling dibs on any worthwhile woman in this town. Should I drop my code and just find out if they are actually interested? Where do I draw the line? Even the married ones drop hints about relationship dissatisfaction.

A: Let’s not get desperate here. As a young, successful, presumably attractive dude, you shouldn't be resorting to preying on women with wedding rings just because you work a lot. 

As is the case with men, some women will always maintain a wandering eye and a “what if” mentality when it comes to upgrading their version of partner. 

These are not the women you should pursue if you're seeking anything beyond a messy and short-lived scandalous affair.

Which, presumably, you are not.

Let's also avoid dramatics, as I find it highly unlikely that the metropolis you reside in hosts no available single partners. That makes very little sense and frankly is probably untrue. 

In order to find them, however, you may need to broaden your horizons. Rather than spending the five hours a week you have free sleeping or drinking beer on your couch, force yourself to be proactive. Take Fido to the dog park.

If you don't have a pet, borrow one. 

Pick up a yoga class (yes, I'm serious) or any new gym class or hobby that requires you interacting with humans of the opposite sex. 

Your 20's are NOT the time to stress about being past your prime or seeking a life partner. So do yourself a favor…and don't.{pagebreak}

More advice on Page 2 …

Q: What is the best way to approach (and possibly sleep with) multiple girls of the same friend group? Is there a “best way”?

A: Sleeping with multiple girls in a friend group could definitely be considered the “best way” TO GET YOUR BALLS CHOPPED OFF.  And never get to bone any of them again.

Take this advice very seriously.

Sure, you might get away with the sexual juggling act for a little while, and it can be pretty cool.

But changing your sheets three times a week, shoving nameless bras under your bed and maintaining iPhone aliases like, “Bob White” and “Jack Jones” can become exhausting – and will eventually catch up with you. 

The day they all figure out your scheming ways will be a dark, dark one for you. 

My advice, if you insist upon sleeping with multiple girls at the same time, is to seek out girls from DIFFERENT friend groups. Avoiding situations where two or more women may bring you up as their lover in casual gossip is a must, so intentionally finding non-friends is key.

Low(er) risk, high reward. And God knows that's what it’s all about.

Q: In your opinion, what is the least acceptable place for a guy to get a boner? If you're with him in public do you expect him to apologize or do you both just ignore it?

A: Public boners are almost always bad news. Unless you're having spur-of-the-moment sex in a privately public or publicly private location, which is generally actually good news.

I'd prefer a guy just didn't pop one in inappropriate situations, period. It’s fucking awkward and I don't want to have a conversation about it. Once you pass puberty it’s just sort of like, control your shit. It’s not attractive when a guy doesn't have a handle on the position and whereabouts of his own dick so if you encounter a situation where you have to tuck, do it stealthily and without discussion.

To answer the actual question, I think standing at the altar would be a pretty RUDE place to pitch a trouser tent.