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Dear Dave and Andy,
I did something really really bad, and I need some serious advice. So I have been in a relationship with a guy for a pretty long time now, about a year, and we are pretty serious about the relationship. I care about him a lot and he always makes me feel happy when I am with him. He is kinda the perfect boyfriend, which leads me to saying why I am extremely stubborn. About two weeks ago I was out with my girlfriends and went to a party, where I hooked-up with another guy! I have no idea what I was thinking and I regret it so much, and to make the situation even worse I know he is planning something special for Valentines Day. Last year on Valentines Day, we had just started dating and we didn’t really do anything too big or extravagant, which is why I know this year is gonna be important to him. I know what I did was wrong, but I don’t know what to do now. Should I tell him now, or wait, or not tell him at all? I’m really confused and I need your advice!!!
Sincerely,
“Sticky Situation”
Dear “Sticky Situation,”
At first we thought we had been stumped; this situation has no right answer or “safe” choice. Fortunately for you though, we have come up with some words of wisdom (hopefully). The fact is he does need to know – it’s only right and fair to him – so that cancels out one of your solutions right off the bat. The main question now is: should you tell him before the big V-Day surprise, or wait till after all the lovey-dovey events? In our joint opinion, we are going to have to say tell him before Valentine’s Day. The reason being, while the events he has planned are important to him and you don’t want to ruin that for him, it could be way worse if you wait till after. Seeing as how important this is to him, he definitely cares about you a ton, and if he feels used in any way, it will really grind his gears. Knowing it happened before V-Day and you waited a few weeks to tell him after the holiday will make him feel like just some boy-toy that you don’t really take seriously.  As much as we would like to say it wouldn’t happen, there is inevitably going to be some tension from this discussion, and you don’t want to add to that by making him feel used or devalued. Lastly, just a side note, you are definitely going to want to do this in person; a face-to-face discussion is the most appropriate and respectful way to handle this. It goes without saying that Facebook statuses, Tweets, SnapChats, Instagrams, yada yada yada all do not count in any way as face-to-face contact. As much as it may upset him, at least you will know you were as respectful as you could have been in breaking the news. We trust that you can work through this together and figure things out, but if you need any more advice (which is very likely), feel free to let us know whenever.
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Your hometown minds of reason,
Dave and Andy
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Please submit all questions, issues, inquiries, or dating problems to: Askdaveandandy@gmail.com and we will get back to you with some top-shelf advice.
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