He’s Got A Good Opportunity With A New Lady – But Is Overthinking It | Doc Love - Dating Advice For Men

He’s Got A Good Opportunity With A New Lady – But Is Overthinking It

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(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 just started reading your articles. I have to say you really know what you’re talking about. I ordered a copy of your book today but I could really use some help because I’m about to get myself into a tricky situation this weekend.

I met Celestria at a bar a week after I broke up with my girlfriend. The first time we locked eyes there was a spark. We started talking and found out we have a lot in common. She is a great girl, smart, funny, pretty and has a good job as a kindergarten teacher. I really enjoy her company and I’m very attracted to her. We exchanged numbers and eventually went out for a few drinks. Things have been going good, but slow so far, which is fine with me. I just got out of a long relationship and I needed to reset myself.

Celestria and I have only hung out a few times since we met and two of those times we were out with her friends. I don’t need “The System” to tell me it was a bad idea, but it was either have the friends there or not see this girl at all. She’s very busy and I’m not full of free time either. We also had plans to have dinner, but she canceled twice. Those were big red flags. One cancellation was because her friend had a baby; the other was because she was sick. Both excuses were true, but Celestria could have made the dates if she really wanted to.

What bothers me is that she has baggage and I think I might be wasting my time. I won’t drag this it out with all the details; let’s just say Celestria’s had a rough couple of years with her family and an ex-boyfriend. Because of what she’s gone through, she has a hard time trusting new people, especially new men. I admire her honesty and I can relate to what she’s gone through as I have gone through similar things. This is why I’ve hung in with her.

It seems like Celestria’s Interest Level is somewhere around 40%, considering she has avoided hanging out with me alone. I think her low Interest Level has less to do with me and more to do with her baggage. I think she’s perfectly happy being single and is avoiding any kind of relationship. I think she’s kissed me because she really does like me though.

Anyway, here’s the situation. This weekend my friend is having a party. There will be a girl, Katie, at the party who is in a similar situation as me (recently free from a long-term relationship) but she’s interested in meeting me. The catch is that Katie knows Celestria. So hooking up with her will certainly kill anything I have going with Celestria.

I don’t want to invite Celestria to the party because that will just be another group date. I like her, but I don’t want to blow off a good opportunity with Katie only to be messed around more by Celestria. What should I do?

Brendon - who’s never been so confused


Hi Brendon,

First of all, I want you to look at what you did here. You read a couple of my articles, you didn’t find anything you disagreed with, and you ordered my book because you know you’re going to get more great stuff from it. I want to congratulate you on being open to improving yourself and your love life. Ninety percent of men out there could read a hundred articles but they wouldn’t study my book if I gave it to them for free. And that’s why they’re in the condition they’re in when it comes to women.

That said, you still have a lot to learn, my friend. Look at what’s happening with Celestria. Let me explain something to you. You don’t know what you have in common with a lady after just one encounter. What you have in common is nothing more than physical attraction. That’s all. And how do you know she’s such a “great girl?” You just met her, didn’t you? So how could you possibly know? She might have a good job, but how does she function in romantic relationships? That’s what counts. Sure, you’re attracted to her – but how attracted is she to you? Is she really available? Those are the critical questions.

When you saw that all of Celestria’s friends were hanging around, you shouldn’t have seen her at all. That’s your problem here, dude. You went along with a bad arrangement from the get-go.

Don’t rationalize this mess because you’re both busy. If this girl can’t find an hour and a half for lunch in the seven days of a week, something’s wrong. Now let me get this straight. Celestria cancelled two dates on you in one week? You mean she broke one date and you went back for more punishment? What’s wrong with you, Brendon? Man, you do need to read my book, and fast, especially the chapter called BROKEN DATE. And by the way, those weren’t red flags you were seeing – this girl’s OUT. PERIOD. I’ve been on hundreds of dates and have never broken one. Who cares if Celestria has baggage? She breaks dates! That’s all you need to know. She’s already history.

Brendon, you are rationalizing up a storm here when you blame this impasse on Celestria’s family and ex-boyfriend as opposed to LOW INTEREST LEVEL. If you were Brad Pitt, do you think her family and old boyfriend issues would be a problem? Heck, she’d say “Oh please can we have some more champagne, Brad?” And if this girl has a hard time trusting new men, she’s UNAVAILABLE. She’s a basket case. Next!

But you admire her honesty. You’re dying to admire anything that’s not bad about this girl! But she’s 90% bad. So why are you “hanging in?” You’re not a psychiatrist, are you? You want to be this woman’s boyfriend, not her counselor.

You estimate Celestria’s Interest Level to be around 40%. The problem is that it has to be at least 51% in order for this thing to have any life. So here’s the important question: why would you go after a girl who doesn’t want to be alone with you? And of course you go and rationalize again that it’s her baggage that’s inhibiting her. It couldn’t be you – because you’re perfect, right? But if Brady Quinn came along, I’m sure she’d find time to play touch football. But you’re convinced that she kisses you because she likes you. Pal, this is called grasping for straws!

Now, on to the big party. It’s fantastic that this new girl, Katie, knows Celestria. Why are you fretting about killing anything with Celestria? You have nothing going with her! Brendon, you have less than zero going with this girl. So if I were you, I’d invite her along and then work both her and Katie. Think about all the fun you can have going back and forth between the two. Maybe you can even get some sparks flying. And don’t worry about being on a group date. You’re finished with Celestria. So just invite her anyway and make the new girl jealous.

One more thing: the minute my book arrives, start reading and memorizing.

Remember, guys: never try to keep someone who doesn’t want to keep you.

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