Sadie will first see Roland during her graduation party in New York although she won’t officially meet him until a few days after. After their official meeting, Roland’s capers should appear in New York as well as all of the exotic locations. To ensure that you stay on Roland’s path, make sure that you do both the capers that involve his storyline (they’ll be labeled as “Story Roland: The Main Adventure”) and the capers that have to do with Sadie’s main storyline (they’ll simply be labeled “The Main Adventure” and have Sadie’s facial icon). You must complete them for New York, Egypt, Australia, and India. At any point, if you miss a caper, you will lose the option to begin a romance with Roland so it’s important to do them.

To have the option to begin a romance with Roland, you need at least 30 relationship points by Christmas. By completing Roland’s capers (you don’t necessarily have to pass all of the obstacles associated with them unless they’re marked in red on the country map), this should be doable.

Once the Christmas holidays arrive, you’ll have an option to spend time with Roland. Do so! It’s the only chance you’ll have to begin a romance with him. During that holiday, you can build relationship points with Roland and then you will have the option to begin a romance with him. Again, do so! If you don’t, then you’ll only have the option to build friendship with him.

Once you start a romance with Roland, your “dream of family” will change to “dream of Roland” and your starting value will be at zero. However, this value will increase quickly by completing Roland’s capers and passing all of the obstacles associated with them. It will no longer be necessary to complete the capers related to the “dream of family” path although you may choose to do so.

Below are the choices I made (marked as “x”) once Sadie arrives in Peru as well as how many dream points I earned after passing certain obstacles. (I’ve done the same for New Orleans and Turkey as well.)

Take a Quiet Moment with Roland (Story Roland: The Main Adventure)

1st obstacle
• Dodge
• Problem Solving x (+7 Dream of Roland)

Adventure with Roland in Peru (Indirectly) (Story Roland: The Peruvian Adventure)

• Can you tell me how many of these pieces would be genuine? x
• These can’t be all real!
• You must be a well-connected man…

1st obstacle
• Moxie
• Deception
• Courage x (+6 Dream of Roland)

• Is this everything you have? x
• I believe you’re still holding out on me…
• Hm…too plain…

• Yes, that’s me. Is something wrong? x
• Who’s asking, if I may ask?
• You must have me confused with someone else.

• This is all just too weird. I think I need a break.
• I have so much to do today. I’d really better keep going. x

• Can a lady refuse?
• What is this about? x
• I’d really rather not.

• Surrender (and miss out on anything you might gain by resisting).
• Resist. x

2nd obstacle
• Fisticuffs
• Dodge
• Strength x (+6 Dream of Roland)

• You can explain right here, I think. x
• Is this another one of those instances when I need to not ask too many questions?
• So what’s the plan, really?

• A lot, I think.
• Not a lot at this point! x

• So what choice do I have?
• I shouldn’t have trusted you. Every time our paths cross, there’s trouble.
• And this is where you tell me something crazy and we hope everything will turn out okay? x

• Yes. x
• I don’t know…

• I’m ready…I hope.
• This is insane! I can’t do this!
• You really think this is the best way? x

• You shouldn’t. It’s not like I trust you.
• Because I have the skills you need right now. x
• The real question is why should I trust you? You’re obviously the larger threat right now with all those guns around.

• Where are we going?
• You mean you’re winging it? x
• Is there a way Owney Madden won’t need me anymore?

• We could just turn him in?
• We could ditch the place and go somewhere safe? Just leave all this behind? x
• We could wait and see what happens?

• You’re the one who started the whole charade. I just need you to take it one step further. x
• It’s the only thing that makes sense. Like dealing with arrows—if you pull them out, you’ll cause more damage, but if you push it through, you’ll have a clean wound.
• All right, yes, I’m joking. At a time like this. When my life hangs in the balance.

3rd obstacle
• Listen
• Perception
• Courage x (+6 Dream of Roland)

• Understood…
• How do I do that? x
• I don’t want to be shot at any more than you do.

• Never thought otherwise! x
• I’d rather stay in the car…
• This guy looks dodgy.

4th obstacle
• Problem Solving x (+6 Dream of Roland)
• Moxie
• Patience

• We’re done here. Let’s go.
• What is the meaning of this? x
• And did you include the glue with all these shards?

• That’s…encouraging…
• I think I might be sick.
• At least we got the goods. x

• But I’ve been alone with you… x
• But we’re old friends…
• I’m absolutely certain nothing like that will happen.

5th obstacle
• Problem Solving x (+6 Dream of Roland)
• Poise
• Stealth

• Sometimes. x
• All the time.
• Only in times like this.

• W-why’s that?
• But it’s so nice here. x
• I haven’t had my dessert yet…

• O-oh. Here. But I haven’t done anything. This must be a terrible misunderstanding.
• May I ask who has been robbed?
• Can I see some identification, officer? x

• Sir? Did you find the thief? x
• Sir? Did you happen to hear who’s waiting for me?
• Sir? Is that all?

• Please. Just once…Tell me what you really want to say. x
• Just here in Peru?
• One day, you’ll tell me why all this happened. Why it makes sense.

Below are the choices I made for Valentine’s Day.

• I was beginning to worry!
• Are you all right? x
• I might forgive you…for a price.

• Uh, no, I haven’t. x
• There’s a Broadway version of Dracula?
• Wait, didn’t Lon Cheney die?

These are the choices I made after Sadie arrives in New Orleans.

Hang around with Roland (Story Roland: The Main Adventure)

• Let him win. He’s so cute when he’s self-important!
• Never give up, never surrender! Pull out the big guns! x
• This game is silly.

Adventure with Roland in New Orleans (Story Roland: The Adventure in New Orleans)

• So…what brings you back to America? Is it just the…bear thing?
• Are you sure you’re okay? x
• Let me take a look at you…

1st obstacle
• Diplomacy
• Moxie x (+7 Dream)

• Press him for details. x
• Try to find supernatural help.

• What does it feel like?
• So you’re saying all this started when you came to New Orleans? x
• How sick are you? I need to figure out how much time we have.

• Not on your life! You need my help!
• What’s wrong? What do you mean ‘baggage’? x
• What did you do to me?

2nd obstacle
• Fisticuffs x (+7 Dream)
• Awareness
• Courage

3rd obstacle
• Listen x (+7 Dream)

• That’s not the help we need!
• Isn’t there another way?
• Stop it! You’re killing him! x

• I need to keep going, Roland really needs my help! x
• I really just need a rest…

• I’ve come across more magicky stuff in my travels than you have, spy boy.
• Why’re you trying to stop me? x
• Is that the fever talking?

4th obstacle
• Diplomacy
• Empathy x (+7 Dream)

• You don’t even know what you’ve gotten yourself into, Ranakdevi.
• You’re bluffing.
• Why Roland? x

• You had me followed?
• You really are, um, magical?
• How does it work? x

5th obstacle
• Negotiation
• Tolerance x (+7 Dream)

• Test me! You have ways to do so, don’t you? See if I’m lying, I dare you to. x
• Why would I lie to you at this point?
• I think the loa lied to you.

• I have no idea what to do while I wait. I guess I’ll come back later…
• I can’t just wander off. I’ll stay close to the shop, just in case. x

• Yeah, I had a few words with her earlier, at Tulane. It wasn’t exactly reassuring. x[/b]
• I cannot imagine how it might’ve been, carrying all her anger around New Orleans…What to do…?

• I’ve been wondering…We keep talking about TWO loa riding Roland. What is the other one? How did it get there? x
• What happens if I’m unsuccessful in this?
• What happens if I’m successful and the loa comes to me?

6th obstacle
• Problem Solving x (+7 Dream)
• Awareness
• Courage

• I’m sorry it didn’t work… x
• But at least it won’t hurt you any more, right?

These are the choices I made for Easter although, unlike for Ahmose’s and Felix’s paths, there was no obstacle to pass.

• Work!
• Traveling. x
• School.

• Military.
• Transportation
• Businessman! x

• Meeting me!
• The job.
• Family? x

Again, these are the choices I made.

Drop in on Roland (Story Roland: The Main Adventure)

1st obstacle
• Stealth x (+7 Dream)
• Escape Artistry

Adventure with Roland in Turkey (Story Roland: The Turkish Adventure)

• What can it hurt, right? x
• There’s obviously nothing here…

• I don’t think I follow. What is this place? x
• Wait, I’m dead but I’m not dead? That doesn’t make any sense.
• Why didn’t some voodoo person tell me that this could happen?

• I bet I can guess… x
• I have no idea…

• Devious…?
• You’re so wrong about him. And me. x
• Is this what I really think? Deep down inside?

• In the end, he did come back for me. He always did.
• I know he brought them down. I’ve seen the proof. x
• He’s not like that, not tempted by power, and he already has wealth. Why would he need to be the head of a syndicate?

• Oh, go to hell, Roland!
• Roland? Is that you? Have you made it? Is this your memory? Roland? x
• This can’t be the truth…can it?

• It’s really very simple, isn’t it? I follow my heart. x
• It’s all lies…unless it’s all the truth? I’m so confused!

1st obstacle
• Problem Solving x (+7 Dream)
• Awareness
• Perception

• You’d leave me here, just so that you can get to the Original Ankh…After all we’ve been through…you would leave me here…just like that?
• You’re not Roland. Roland would never leave me here like this! x
• There is no way I’m just going to sit here and take this.

• You’re…you’re not Roland. Th--There’s no point in trusting you. It doesn’t prove anything.
• I’m not playing anymore. x

• Sadie needs to stop whining, and get to the point! x
• This hits home. There’s someone in my life I’m not sure I trust either.
• Um. What’s going on?

• Sadie: ‘Was that the sky I saw for just a second there?’
• Sadie: ‘Something big is happening, I can feel it.’ x
• This is so meta.

• Yes!
• No. She’s got to use her memories! x
• Aw, menu item #2 gave it away!

• I…don’t understand.
• I’m not that important. Or that good.
• But everything we did just led to more retaliation. x

• Shut up, other Sadie! I’ve just had about enough of you.
• No, I don’t know ‘what would happen.’ All I know is that all he’s ever done is try and do the best he can. x
• This is getting far too weird.

2nd obstacle
• Courage x (+7 Dream)
• Self Knowledge

• Raze the world!! I am all-powerful! Bwahahahaha
• Take power, so I could help whoever I could!
• Keep it safe from everyone, even from me. x

• It’s so peaceful here…
• I can see the sky again… x

• Hey you did pretty well too, if you don’t mind me saying so. x
• I wouldn’t say I’m ‘untarnished’…
• What about you? Are you okay?

Following these steps, I was able to achieve 100 “dream of Roland” points and see his best ending. It’s quite romantic although I must admit that the ending does have me a bit confused. (I won’t reveal what it is since that’s clearly a spoiler). As with the other paths, you need to pass all of the obstacles. As before, I didn’t state what the point values were needed for passing obstacles since they may differ depending on the difficulty level. However, if you raise your stats well and obtain good inspirations, you can pass all of the obstacles and get the best ending.

Again, if there’s anything I’ve missed in this walkthrough, please comment below and I’ll make the necessary changes. I hope this helps for everyone who’s wanted a Roland walkthrough. ^^