10 Years??? | Doc Love - Dating Advice For Men

Dating Women Advice: Would Jake Gyllenhaal Ever Look Up An Old Female Classmate?


It's been 10 years and he's thinking there is a chance?  Yes, there is - but it's a VERY slim chance - read the article below and...

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Dating Women Podcast #61 & 62

Your article is right below this but first on this week's podcasts we give you:

*61:  Is her schedule too busy for him?
*62:  Is his moving away for grad school too much for her?

Hit the "listen now" link below to get these shows and connect to all of my podcasts (growing weekly!)

PS - if you want even more audio - listen to our weekly Dating Women Radio Show (Wednesdays at 5:00 p.m. PT / 8:00 p.m. ET)


Hey Doc,

I’m a single guy in his early 30s. For the last decade, I’ve thought about Dina once or twice a year and wonder what’s become of her. We met 10 years ago when she was in my college economics class. She was very attractive and we would make occasional small talk before class. She always made the effort to greet me pleasantly and say hello anytime she would run into me. At the time, I had guy friends who noticed and called me an idiot for not courting her, as it was obvious she had genuine interest in me. My excuse then was that I was not interested in dating because I was focusing on my studies and getting my stressful life in order because I was a poor college student. Now I’m a successful career professional and would love to genuinely date Dina and get to know her family – if she qualifies according to “The System.”

I did a few keyword searches online and found Dina’s profile on a social network website. I felt a beautiful sense of awe and nostalgia as I skimmed through her profile and images. I learned that we are the same age and she seems to be totally single at the moment and just waiting for the right guy. She currently lives in another state, but divides her time between there and her home state to visit family. I currently live in her home state, but plan to relocate in the future coincidentally to the state where she currently lives.

Doc, should or should I not reconnect with Dina? If so, how can I do it? Sometimes in life we meet truly special people for a brief moment and catch ourselves thinking about them for many years to come. I believe Dina and I would be happy to see each other even if by chance. So here’s hoping!

Stuart - who can’t stop thinking about her

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BlakeAustin, TX

I may have been able to find her, but I never would have been able to KEEP her without you, Jeff, and the "System."


Hi Stuart,

First of all, you should have asked for Dina’s number when you met her 10 years ago. Like my cousin Fast Eddie Love from East L.A. says, “If you had hustled her at the beginning, you wouldn’t be thinking about her a decade later.” So you made a mistake straight out of the gate, my friend, since as you know from reading my book, the rule is ONE SHOT PER GIRL PER LIFETIME. And you blew that. That said, you now have a different scenario with Dina in front of you, and I will coach you in navigating it.

What you have to realize, Stuart, is that while you have a beautiful fantasy of what Dina is like right now, the image you have of her is from 10 YEARS AGO, and 10 years is a long time. That image may bear no resemblance whatsoever to what Dina is like now. Like my Uncle Jethro Love says, “For all you know, she’s been married twice, divorced and has three little kids.” The point is that you know absolutely nothing about this woman, so you have to be careful not to get lost in daydreams and fantasies that might have no relation at all to REALITY. That’s the danger you’re in here, Stuart.

Moreover, you have to understand that the numerical probability of Dina being available is one in a million. In addition, you’re talking about a long-distance relationship here, and even if you contact Dina now, by the time you actually get together with her where she lives, she could have met somebody else. So what you’re dealing with is an unfortunate combination of going back 10 years and a long-distance relationship. Once again, you’re looking at very unfavorable odds to say the least. The odds that this woman is available or still has interest in you are astronomically against you, like I said earlier.

Keeping all of those caveats in mind, you should go ahead and reconnect with Dina. Email her and tell her that you’re traveling to the state where she lives to do some business. Then say that you’d like to take her out to dinner and catch up. You have nothing to lose with this strategy.

Dude, when you say that sometimes you meet a special person and think about her for years to come, you’re in La-La Land. Had it been 10 weeks or 10 months that you’re looking to leap over, it would be a lot easier. But you’re talking about 10 years – that’s a long, long stretch of time.

And why aren’t you dating local women, Stuart? Why aren’t you out there hustling the phone numbers of women around you and in your neighborhood? Like my cousin Rabbi Love says, “You’re getting all wound up over something that may very well turn out to be nothing but a pipedream.” And let me say again – the odds in this situation – that Dina is available, and interested in you, and that she doesn’t already have kids or was married -- are very much against you. No offense, guy, but you have to read and memorize “The System” to straighten your head out because your betting odds in this poker game are terrible.

Remember, guys: the chance of successfully dating an old flame from 10 years ago who lives far away are slim to none.


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