Real Live College Guy Joe: How to Leave Things Before Winter Break

Ever wonder what guys think, how to deal with them, or whether instead of listening to you they just imagine you naked?  Our Real Live College Guy Joe will answer all your questions about men and relationships with wit, clarity, grace, and physical attractiveness (can you tell he wrote this intro himself?) all while imagining you fully clothed!  Well, usually – he is a college guy. 

I don't have a boyfriend, but I have a few guys on my radar, who I've either sort of started to date, of have hooked up with, or have just been flirting with, etc., all of whom I think have potential for something.  But now it's about to be winter break and we're all going to be in different places for a month at home and not at school!!  How should I leave things before school ends and then what can I do over break so that those don't all fizzle by the time second semester starts? –Bubbly at Bowdoin

It sounds like you're in a very lucky position, Bubbly.  Either women are scarce up at Bowdoin, or you're much more attractive than your fellow female classmates, most of whom are probably moose. 

Regardless, the answer to your question is pretty simple.  When the last days of finals roll around, give each guy a little something to hang onto and tell him you look forward to continuing your relationship in the spring term.  Of course, this differs depending the on the relationship you've had with each guy:

• Started to date: Go on another date, but this time make it more special than all the rest.  Wear your sexiest winter parka.  Get the best mutton in town.  Or eat in; maybe you cook his mutton, and afterwards you really cook his mutton – you know, if he likes it well done.  Anyway, make the date extra nice so he'll have something to remember you by aside from your pleasant lack of antlers and fur.
• Have hooked up: Hook up with him again, if you feel like it.  But, again, go a step further.  If you've just made out, maybe take it up a base.  If you've already gone around the bases, then maybe go around them running backwards (if you figure out what this means or how to do it, please let me know).  With a little late-night lovin', he will be more likely to think about you during break, or spend break perched longingly outside your bedroom window.  The BEST thing you can do, though, is to buck up and go on a real date, even if you have to ask him.  Then he'll know you're serious. 
• Just been flirting: Similar to the previous two scenarios, in this case I would advise doing something sweet and serious, such as a date.  Don't make it anything big, just coffee or a movie or a visit to the museum with your parents and entire extended family.  He'll see that you like spending time with him, and, if he likes spending time with you back, he'll be primed for continued courting once frisky springtime rolls around.  And, like I say in almost all of my columns, you should TOTALLY feel free to take the initiative and invite him on these dates.  As much as the thrill of the chase is exciting, it may not be clear that you want to pursue something further.  So go ahead and invite him; hell, pay for the meal while you're at it!  If only…

So now it's winter break.  You've left things well with all your potential mates, and you've gotten as far away from Maine as you possibly can.  "But what to do now?" you ask yourself as you bask in the sun.  "And what is this bright orb that creates warmth and melts away the snow?" 

During break, make sure to keep contact with whatever guy(s) you're still interested in.  Hopefully, your process of post-break dates helped you weed out some of them – the weak from the strong, the well-fed from those who wouldn't last a blustery Northeastern frost – so you don't have to keep playing coy to lots of guys at once.  Either way, make sure you're texting them a lot with jokes and cute nothings and updates on your menstruation cycle or whatever, maybe even call a few times.  Once again, don't hesitate to send the first text or make the first late-night call.  He'll appreciate it and should return the favor; if not, cut him out of your life like a frostbitten toe on a long day-hike. 

Once you're back at school in the spring and realize that there are really still seven months of winter to go, get in contact with him, pick up where you left off, and make sure he didn't put on more weight over the break than what he needs to keep warm.  Then you can resume your process of seeing which relationships have the most potential, at which point you'll be writing your trusty ol' Real Live College Guy about how to choose between two equally-winning Bowdoin gentlemen, one skilled in bear-trap-setting and the other in igloo-building.  But that's for another day.