Without too much rehashing, this is someone I have known for 10+ years and have had crazy feelings for for more than half of that time. Since we have always been friends first and had major timing issues (living in different states/cities, being single at opposite times), it’s always been complicated for us to tell each other how we really feel. Still, he broke my heart once when we were kids and I feel like I can’t be sure of where he’s coming from. Any thoughts? — Fantasy Girl Next Door
DENNIS: It sounds to me like he’s crazy about you. I understand your hesitation, since he did break your heart once. But whether or not it’s time to forgive him depends on how you define “when we were kids.” Are we talking high school? Junior high? Kindergarten? I mean, I certainly hope I’m not accountable still for the stuff I did to the girls I liked as a kid (you know, hair-pulling, loogie-hocking, spitball-throwing, “kick me” sign-taping to the back, etc.). If I were, I’d never be able to get a date today. I certainly hope I’ve learned to treat women with more dignity since my days of cootie accusations.
My point is, you two grew up together. I just can’t imagine him saying what he did without meaning it, and I think you have to give him credit for having matured over the past 10 years. If nothing else, think about what he said: You’re his fantasy girl that he wants to end up with. I’d say that last part makes it pretty clear whether he sees it as a fantasy or as true feelings.
BITTER GAY MARK: Question 2) It means you should grow a pair of balls and ask the poor guy out. Could he possibly be any more directly indirect? As you say, this guy clearly isn’t a player. So, you have a long history with him, but the timing is often off… Hold on a minute, Sally? Is that you? Seriously, what is The Trouble With Harry? You want this guy. He says you’re his “Fantasy Girl Next Door.” Wait, what’s the problem? Oh, right. You’re worried about him breaking your heart. (Again.) Newsflash, he already broke your heart once — and guess what? You survived it!! Sure, having your heart broken sucks. Guess what sucks even more? Wasting your entire life pining and longing for somebody who is literally wasting away doing the same for you! You have nothing to lose, here. Seriously. That great friendship? It’s not healthy. Not if you are in love with the guy! Go for it!! Don’t let all of your cold feet doom you both to a life of wondering what might have been…
ERIK: I think most guys want to be able to act like friends sometimes with the person they’re dating. It’s rare that someone comes along who can be both a great friend and a great romantic partner. It seems like he’s trying to move your relationship to the next level, but it’s hard to say for sure. If you are interested in pursuing a romantic relationship with him then I’d take that as a pretty good signal that this would be a good time to go for it.
* If you’d like to ask the guys a question, simply email me at email@example.com with “His Take” in the subject line and I’ll pass your question along to them.