She Asked – What Was Your Longest Relationship? How Should He Answer??? | Doc Love - Dating Advice For Men

She Asked – What Was Your Longest Relationship? How Should He Answer???


(Editor's Note, this letter was written before Doc's death in August, 2020 but still relevant as Doc's principles are timeless).

Hey Doc,

I am a 36-year-old, well-educated, happy and successful dude. I am also well-groomed and well-preserved and am thought of as a guy who has his game together. I love your material, and the fact that you are always making sure us guys are being careful at the same time that we’re enjoying the journey.

I just got out of a two-year relationship – and of course she left me! After reading your thoughts on being on the rebound and emotional baggage, I should have seen the “red flags” much earlier!

Anyway, I am back on the love hunt and need some help. I just went on a second date with a 31-year-old “Caprice” after a very successful first date (on which I waited five days to call, made a quick call to set up a Starbucks meeting, no touching, though she touched me several times, kept it to 45 minutes, etc.). She even e-mailed me that night to thank me for a great time.

On the second date I picked Caprice up and took her to dinner, and everything was going great -- until I opened my yap! She asked me a personal question about a past relationship. Nothing too heavy, just “So, what was your longest relationship?” So I thought I’d have some fun with it, and told her she needed to show me a sign of good faith. I proceeded in a very light and funny way to say that if she kissed me on the cheek, I MIGHT tell her. Man, did I think that was smooth! But right away her whole attitude changed, to very closed-off. She even folded her arms at dinner! She told me I should be more open since she was being open with me, and blah blah blah.

Well, I was able to steer the date somewhat back on track after a bit (but still did not answer her question). I dropped her off at her place and tried to give her the “what the hell” kiss. She then leaned over and kissed both my cheeks and whispered, “Okay, there are your kisses, and next date you owe me my answers!”

I smiled, grabbed her by the back of the head, and laid a deep, long one on her. She smiled, with her eyes still closed, and then I walked off. What do you think of my genius move after she kissed my cheeks? Do you think she is worth the all-important third date, or was her immediate closed-off response to my cute cheek-kiss question not that of a Flexible Giver? Anyway, lay it on me, Doc!

Sheppard - who wants to know if he has a tiger by the tail

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Hi Sheppard,

Hey, why are you “well-preserved” at only 36? I thought well-preserved went with being 86 and having one foot in the grave. Are you sure you’re really 36 years young?

You mentioned that I want you guys “enjoying the journey.” Man, I couldn’t have said it better myself. That’s the most beautiful sentence in your letter. Guys, you have to enjoy yourselves when you’re out there dating, and you have to study my book not only because you want to get the girl, but because it is the TRUTH. Like my cousin Rabbi Love says, “My son, the truth will lead you to do some great, great things, if you’ll just let them happen.”

Regarding your ex, Sheppard, I’ll bet you did see those big red flags early on, but like most men you decided to look away, and you rationalized them on account of your high Interest Level. But slowly those ugly red flags chipped away at your level of respect and the end was inevitable – like it always is.


My friend, you did everything right on your first date with Caprice. I’m proud of you. When she e-mailed you to thank you for a great time, that was an indication of high Interest Level. Her gesture was above and beyond the call of duty. So your Caprice was okay after date number one – she showed some traits of being a keeper. But you have a long, long way to go. Like my cousin General Love says, “It will be easier to get Hannibal’s elephants over the Alps than it will be to get this woman to nine dates!”

I’m glad you realize that loose lips sink ships. As my cousin Fast Eddie Love likes to put it, “The problem with every guy is that he opens his yap!” To you Psych majors, once a girl likes you, you should never talk again. It doesn’t raise Interest Level, which is all you should be concerned with.

Caprice probes you about a past relationship and it’s “nothing too heavy?” Dude, this is very, very heavy. This gal didn’t bring a BB gun to dinner, she brought a howitzer! Do you need glasses, Sheppard? Remember, when they start with the heavy questions, you’ve got to channel Chris Rock or Jim Gaffigan on the spot.

Making Caprice kiss you on the cheek as payment for your background information was a very gutsy move. I happen to think it’s too strong for the second time out, but I’ll give you a top grade for closing. At least you had the guts to go for it.


Know why Caprice’s attitude went south? Because she didn’t want to play. Her interview was more important to her than falling in love with you. She had her agenda, and she was going follow it come hell or high water. Like Johnny down at the Shell station, she hauled out her list of “to-dos” – check the tires, oil, air filter, transmission fluid, etc. What she did, really, was give you an indirect ultimatum. And when you didn’t capitulate to it, everything changed -- her body language, her attitude, everything -- just because she didn’t want to play. Caprice doesn’t want to be loved. Her agenda – dragging up all of your past romantic disasters right then and there -- was the most important thing to her, and if it takes any longer than right now, then she’s out of there. Wow, does she sound like a blast!

But good for you, Sheppard, that you didn’t go along with it. Ninety-nine percent of all guys would have caved on the spot and sold out their manhood.

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I have to hand it to you, guy. Going for the “what the hell kiss” shows that you’re a winner. You get an “A” in LIPS. You might be doing some stuff wrong here and there, but when it comes to LIPS, you’re aces.

When Caprice mentioned your next date, you should have growled, “Hey, sweetheart, aren’t you’re being just a little too confident here,” just like Jude Law would have, then flashed your best boyish smile. When you laid the deep long one on her, you showed again what you’re made of. Most guys don’t have cojones, they’re shrinking violets in the presence of these 110-pound sticks of dynamite called females, but you’ve got the opposite problem. I want to tone you down a little bit. But I dig that you walked off into the night just like Humphrey Bogart.

Your genius move worked, Sheppard. But what we don’t know is whether Caprice is Flexible, and, therefore, a keeper. She wanted hard answers to her interview, so you’re up there in terms of her Interest Level. But I didn’t like her pouting – it shows that she’s inflexible. Every time you two disagree on something in the future, she’s going to pout. And don’t forget, this was only date number two. When she starts laying on the guilt and pressure over the big stuff – money, kids, in-laws –you’re going to feel it like a rat being suffocated by a boa constrictor. Man, do you really want that for the next 45 years? That’s what “The System” is about: preventing half a century of mystery when you’re stuck with the same woman. Guys, can you imagine?

So what you’re going to do, Sheppard, is not answer Caprice’s questions. You’re going to come up with “funnies.” When she says to you, “So, what was your longest relationship,” you’re going to say, “I’m still in it. I’ve been going with this girl for four years.” And when her beautiful violet eyes widen and she demands, “Well, what are you doing with me, then,” you’ll say “I’m looking for a replacement. I need some backup. That’s why I’m interviewing you.”

Fellas, like the great Zen masters you have to learn to be detached. Being joined at the hip forever doesn’t work.

Remember, guys: you gotta go for the kiss.

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