So there is a friend of mine whom I’ve started developing feelings for. We started seeing each other more “one on one” doing “date-ish” activities (e.g., dinner and movies, cooking together, etc.) which usually occupy a good chunk of time… More recently, he asked me to have drinks and dinner with him at two trendy venues. I didn’t expect him to pay, as we usually go dutch, but he paid for the drinks (which was probably more expensive than dinner!). I ended up going back to his place and crashing. I’ve stayed over at his place before, but I would usually sleep on the sofa. This time, I slept on his bed, but I tried not to let anything happen as I was quite sick that weekend (not sure if he noticed). The next morning, we had brunch together before parting ways. The entire weekend was a really good time (20 hours of time together!).
Later that same day, I texted him to ask whether he thought of me as just a friend or if we were dating, and he responded a while later with friends and that I wouldn’t want to date him because he is “terrible at it (dating)”. I know I should not have texted him in the first place because now I am left more confused than ever! I do intend to be up front with him on my feelings still, but can you tell me (from what I’ve just described above) why he may show this dissonance? His actions leading up to my (stupid) text indicated to me that he may have wanted something more than friendship… thoughts?
Dear Confused chick,
It ain’t always easy being friends with people you’re attracted to. There’re a lot of pitfalls. Blurred boundaries become the norm. What once was very clear cut because a bit of a clusterf*ck. You’re ready to come clean with him about how you feel and that you’re willing to break those boundaries outright hoping to create some different ones. How can you know if you’re about to set yourself up for a brutal fall or a celebratory fall into the sack?
Based on what you’ve presented, I’m inclined to think that he probably does have feelings for you but he also has no confidence that you two would work out. Some people run from what they want because they get scared. They get scared of learning that they’ll get what they want but then lose it. They’ll get scared they’ll find out they really aren’t ready to get what they want. They back away because they’re scared of somehow failing and feeling like they are less than in terms of being a person. It’s not the healthiest mindset. They deny themselves a chance at being happy for the certainty of a familiar kind of unhappiness. Now, is that someone you are prepared to put your feelings on the line for?
Now there’s also the off chance that he’s just not interested and didn’t know how to let you down easy. Based on the evidence, I don’t know. I feel less inclined to believe it. You don’t usually let a girl sleep in your bed unless there’s a part of you that wouldn’t mind if your nether regions “accidentally” found each other in the middle of the night. I’m sure there are guys out there that have no interest in the girl who sleeps in his bed. He’s probably over 25.
I would say you’re overreaching but I encourage you to overreach. The uncertainty is going to drive you crazy. The times you don’t take a shot are the ones that’ll haunt you for the rest of your dating life. You’ll always have this twinge of regret over not knowing what could have happened. He’s been pretty upfront with what he feels like he can offer but you haven’t given all that you can offer yet. Give it a shot just don’t hinge your happiness on him suddenly going back on his word. Do what you need to do for you.
To thine own self…you get it,
[Got a Dude itch you just can’t scratch? Sick of trying to come up with a not-totally-crazy-girl way to bring it up to your guy friends and get their take on things? Totally over over-analyzing the cryptic messages he leave on your Facebook Wall? We got your back, girlfriend. Send your question over to askthedude [at] collegecandy [dot] com. The Dude won’t sugarcoat it, beat around the bush, or any other weird cliche that means lie to you. Like a nice, juicy hot dog, he’ll be 100% real beef, 100% of the time. So bring. it. on.]