Dr. Date

Dr. Date,

What are your thoughts about timing in relationships?  Is it possible to have met the right person at the wrong time in each other’s lives? 

I ask because I am 20, dating a 26-year-old, and we are at two different places in life right now. I can tell I’m not as mature or wise as he is. He’s the man of my dreams, but I’m not sure if I’m ready for that yet. I just wish I was a few years older before we had met. 

—Tick Tock

Dear Ke$ha,

Much like comedy, timing is everything. And like comedy, when it doesn’t work out at the right moment it’s awkward, weird and horribly unfunny for every person involved.

That said, your situation seems to be come from a simple lack of confidence. You’re intimidated by this guy but, according to you, he represents everything you’ve ever really wanted in a man. And your excuse is you’re not ready for him?

You think Alvy Singer was ready for Annie Hall? You think Rob Grodon didn’t have a million butterflies in his stomach when he first asked out Laura? What I’m saying is these things happen both ways, and it’d be a shame to let some youthful ambivalence get in the way of what could be a rich and lasting relationship. 

—Dr. Date

Dear Dr. Date,

My ex and I have a 5-year age difference — he’s still in college, whereas I am in graduate school and landed a lucrative engineering job.

Lately, he’s told me that no one understands him like I do, that I’m his best friend, etc.

He told me the other day that he WISHES HE WAS ME. He’s envious of my general satisfaction in life, my friends, my house, my job, etc. He said that I’m too good for him because I am nice but not a pushover and always concerned about making good choices whereas he is ultimately an unhappy person.

There is a mis-match right now. He says I am his best friend, but I have a different best friend, and my ex simply won’t ever fill that role in my life. I want to be boyfriends again at some point, but he has a different (on-again, off-again) boyfriend and doesn’t want to date me right now.

I don’t know what to make of that. He was basically degrading himself in front of me and putting me on a pedestal.  In all my years of dating I can honestly say he’s the only person I have truly, unconditionally loved, which just makes hearing him talk like this difficult for me.

Why would he want to BE me, but not be WITH me?  What do I do about him?

—What’s He Doing?

Dear Mindgame Man,

It sounds like your ex is going through a post-break-up identity crisis. These things happen. Fortunately for you, this one seems to be a little more self-aware —

almost to a fault — than most.

Though, it seems that you weren’t just your ex’s ideal best friend, you were his role model. And still continue to be. He wants to reach out to you, but he knows dating you again will do nothing to get him out of the existential rut he keeps saying he’s stuck in.

If you’re still willing to remain friends after all this, he’ll come around eventually unless he’s so miserably morose that he’ll never see straight again. If that’s the case, then this problem clearly transcends the confines of your relationship. 

—Dr. Date

Dear Dr. Date,

I always seem to keep getting knocked down by love.  Whenever I get my heart broken, I get back up again and tell myself that love will never keep me down, but I just feel like I’m pissing my youth away.  Drinking whiskey drinks and vodka drinks hasn’t helped, and neither has singing the songs that remind me of the good times.  Don’t cry for me doc, but do you have any tips to keep getting back up after I keep getting knocked down?

—Boff Whalley

Dear Tubthumper,

My first knee-jerk reaction to this would be to sift through your elementary school CD collection and start blaring Chumbawamba for motivational support. But even for me, that seems too juvenile and easy.

Also, booze won’t drown your sorrows. It’ll only postpone whatever pain is still festering inside you. And this doc knows a thing or two about pain.

Sometimes the fastest and most efficient way to recover is to simply take a break. Step out of the game once in a while. Decompress and then look again but only when you’re ready.

And just in case this is an issue, stop scouting for guys at bars or parties. I don’t need to explain this.  

—Dr. Date