I apologize for the skill bars, plumbob, and low quality images in advance. I am still getting the hang of this. Italicized sentences are my words, regular sentences are Don speaking, bold lines are his thoughts, and colored terms are the words spoken by other characters in the images. The bold colored sentences are their thoughts. If there is an asterisk next to a word, there is a link at the end of the post to explain it better just in case someone is confused.
And so begins the story of what this simmer did with Don Lothario...

Hello, Don.
Are you going to torture me like a lot of other omniscient beings?
That depends on what you consider torture. I rather think you will enjoy what I have in mind.
Really? Bring it on, then.

All right. Well, since you're already in such a good mood and have a reptile-themed car (which so much could be said about, but I'll refrain), how about going for a ride and visiting some Sims in the neighborhood?
Lady sims?
Yes.
I'm liking where this is going...
First stop, Constance Shelley...
What am I doing out here? I really should get back to my writing...
Sooo, Constance, I hear you're in Journalism...

That's...exciting...

Sooo, are you single?
No time for chit-chat, Don?
No! I may be a young adult, but you only have me on the regular lifespan!
Which is still 90 days...
And I'm already 30 days in!
Yes, I'm single...
Why do you ask?
Well....

I'm sure we could write beautiful tragedies and comedies together...
Errr...
Are you flirting with me?
Yes.
Yeah, not working, buddy.
Well, how would you like to have my pen dip in your--
WHOA, hold on there! What kind of girl do you think I am? I think you should leave now...

What a prude! Well, let's see if I'll have more luck here...
And whose house is this you may ask?
As if I didn't know what your lifetime wish was already, Don. Well, there it is, readers, for those of you who do not know what his lifetime wish is, as I pan around to the other side of the door...
Yes, Don, we know now.Nice house you've got here, Lorraine.
Isn't it just? Purrrfect for a mayor-to-be, don't you think? Well, it IS a bit small, but I can always add on later or move into one of those lovely homes on the other side of town.
Have you read any Sherlock Holmes books? Such spectacular characterization in The Sign of the Four! I wish they had been able to keep the treasure at the end, though, I think they deserved it.
Great, another bookworm, just what I was looking for. 
Um...okay?

Are you single, by any chance?
Well, that's out of the blue, but I will need a trophy husband and he might do...
Yes, I am, in fact! Do you see any dirty socks on the floor?
Well, in that case...

Do I make your flags flutter, baby?
Maybe a little... though more like those butterfly wings on the furniture...
He may need some grooming for his manners to be my trophy husband, but at least his beard is well-cared for. And I don't see any nose hairs...
Oh yeah, she digs me. Lean in, baby, and gaze upon my handsome face.
So can I use your picture for my non-existent computer's background?
No, sorry, can't risk my reputation being ruined before I even get to the top!
Oh well. I'll see you around then, I have some other neighbors to visit.

Hellooo, beautiful.
His house probably has the cheapest furniture. It wouldn't be worth it.

So, what do you do for a living?
Oh, I run errands for a company.
So you're a delivery boy*? Well, woman...
...Sure, let's go with that.

Well, you must be doing well, that's a great house!
If he only knew...So, do you live in there all alone?

And who's this square?
About time someone noticed me back here...Heeeeeyyyy!!!
Did he just call my brother a square? If only Ma knew...
Nah, I don't live on my own. That square is my brother, Sherman. We live here with my mother.
Although if you're asking me if I'm single, I am. 
Well, what would you say if I told you I want to get my tentacles all over you?
Well, it has been a while...

We don't have any weather because the clouds wouldn't dare mar your loveliness.
That's...
Actually not so bad...
Time to get a move on, Don, there are a couple of other ladies I think you want to meet before the end of the day.
Of course.
I don't see any ladies here. Just a lot of plants.
Erm, Don, you see that tall green thing with a pink flower between the bushes and the garage? That's your lady.
Oh yeeeah, now I see her!

Hey, didn't see you there when I stopped by. The name's Don Lothario, I'm new in town. Got any pointers for me about the place?
He didn't see me? How could you miss the blonde hair?!
Suure, Don. I've got to wash up though, since I've been taking care of my plants all morning. I guess you could come in.
It's plotting against me, I swear. Only IT would do something like this...
That tomato plant must have been waiting for me to turn my back before it decided to let the fruit out. The sunflowers probably let it know I was in here...there's no other way it could have found out!
So what do you do for a living?
Fertilizer analyst.

So that's how you have such a nice house...so...bright...
Not really. I don't get paid that well. The government gave my parents money to get me out of their house so I could perform top-secret experiments for them with plants where I merge Sim DNA and plant DNA. I'll call them...Plantsims!
Okaaay...

Sooo I'm guessing you're single?
How did you knooow!?
Lucky guess...

Did you paint these walls yourself?

Because they suit you, the bright colors, the haphazard arrangements of the strawberries...
In fact, the red paint is so similar to your lips, it makes me want to...

Kiss you...
Oh, my...
That's even better than Hunter's first pick up line back in high school! Of course, that was before he began thinking the world was going to end. Heh, the world ending...he must be crazy.
Well, if you want to know about the neighborhood, I can recommend stopping by the art museum.
I mean, there's no Mona Lisa--
But the jars are pretty cool! Not that I'm much of an artist, I prefer going to the concerts over at the theatre--
But I remember on this one field trip there, one of the statues talked to me! It told me all about where it had been and what sorts of things it had seen at the museum and what the workers did after hours when they thought no one was looking! I'm sure it would tell you, too!
Well, that's very nice and I'll keep it in mind, but I should be going. I still have to introduce myself to some of the other people in town. See you around!
Scared of her Don? I guess you won't be trying to use your wiles on her again.
Who said that? Just because she's crazy doesn't mean she's out of the running!
She isn't crazy, she's creative. On to the next, then, I suppose...and it seems to be getting dark, so you had better get going.
Yes, Don, we KNOW.
Doesn't hurt to have a reminder once in a while. Wait-this isn't the one I was looking for!
You're complaining?
Naw, just a surprise. Let's see what happens...
Oh, hello, are you new in town?
As a matter of fact, I am. Don's the name. I'm going around to meet the townspeople and get some recommendations about what there is to do around here. And you are...?
Shirley. Come on in, I think I have some brochures about our little town and some of the attractions...
Speaking of attractions...he's got a nice backside...and I got to meet him before Roxie!
She's checking me out, isn't she?
It seems so.
Perfect...
She's not too hard on the eyes, either. I was hoping to meet the sister I've heard rumors about from the McDermotts, but this might be interesting...
So do you work in town?
More on the outskirts, actually. I work at the hospital. Why don't we talk over by the stairs? I don't think either of us wants to catch a cold hanging out over here by the glass doors.
I wonder...
She's checking me out again, isn't she?
Yes, she is...though perhaps a bit more thoroughly than before...
This one will be easier than I thought...the rumors about her must have been wrong.
Well, we shall see, won't we?
He's coming closer!!

You've got a pretty nice house here.
Oh, this isn't "my" house really. This is my sister's half. I'm on the other side. It's much cozier.

Since you and your sister live together, I'm guessing you're single as well?
So he knows about my sister, already, huh? Well, she does have a reputation. But I'm sure I can convince him I'm the better choice.

You'd guess right! I'm completely single and available.

In fact, I'm so single that it's practically a crime!

It definitely is a crime that someone as beautiful as a movie starlet is single. How would you like to go out with someone else who has movie-star looks such as myself?
Whoa, wait.
Ego much? You may be attractive, but you're not movie-star attractive.
Ouch. Just...ouch.

How could you say such a thing?

I was even asked to be an extra in a movie!
Yeah, right. In your dreams, maybe.
How about just going to the movies sometime, then?
Forget it. Extra or no extra, I'm not going to date someone so egotistical.
At least not without getting to know them better.
It's a shame he has such an ego, though. He's not that bad-looking. Maybe I was a little harsh?
Oh, is that the time? My show is on!

I love this show. All those women fighting for that one guy. And they think he'll fall in love with one of them with all those others around. It's hilarious!
Yeah, it is pretty messed-up.
But don't you think that, once in a while, it does happen?
Uhhhh...

Not really. I mean, speaking from a guy's point of view, he may be in lust with a few of them. But love? Naaah, not like such a thing exists, anyway.
Is that so...
Seems you think like my sister. Some making out on a bench and you're good to go.
Well, not good to go exactly, I would hope there would be more than that, but yeah, pretty much.
I see...well, it's a commercial break. Maybe you could get home before the show ends.
Will your sister be around tomorrow?
Maybe.
I'd like to meet her, so I'll be stopping by in the morning.
I won't be here.
Well, Don, was it a successful day in your estimation?
Oh yeah. Met 5 hot chicks. And more tomorrow, right?
A few, possibly.
All riiiiight.
And so, Don Lothario dreamt about himself all night...
And his fear of commitment...
Alllll night.