Natalie "facts"

[Aikiweezie]

Can't remember if I jumped in on this one before but........I haven't given Natalie much thought because we know NOTHING about her other than she broke up with Trip in a "Dear John" letter and that Archer knew about her (THE Natalie from Pensacola?) Now that I'm thinking it over I guess I don't think breaking up with someone like that is very nice, but it's better than stringing them along while you're cheating on them or looking for someone else to be with. Assuming that's her motivation. Why would archer remember her? Maybe she was gorgeous. Or wild?

As far as Trip being a regular guy and a gentlemen....I think Trip is a regular guy who thinks he's trying to be a gentleman, and is frequently unsussussful. Yup, he was a jerk to T'Pol in the beginning. Not very gentlemanly. Yup, he did try to get some alien action (and was successful as far as I can tell with Princess Fishstick), typical for MOST young, single guys.

Not sure I would equate Trip's rage against the Xindi as gentlemanly or not, though. The writers went a little "Captain Ahab" with that one, I think.

[Pegmumm]

My question always was... in "The Crossing" Trip mentions going sailing in New Zealand with Lisa. Who was Lisa?

One can only have one primary relationship at a time. It was always my impression Trip's primary was with his warp engine.
There really wasn't much of anything said of Trip's relationship history. Everything is fair game. She can be whomever and whatever you want.
peg

[Aikiweezie]

My question always was... in "The Crossing" Trip mentions going sailing in New Zealand with Lisa. Who was Lisa?

One can only have one primary relationship at a time. It was always my impression Trip's primary was with his warp engine.
There really wasn't much of anything said of Trip's relationship history. Everything is fair game. She can be whomever and whatever you want.
peg

I thought he said somewhere that "Lisa" was his high school girlfriend. In "Breaking the Ice" he tells T'Pol that he only had three relationships and all of them "went bust." Can't remember if that was brfore or after the Natalie breakup, but pretty sure it's before. I'll try to confirm that.

[Alelou]

We know very little about Lisa. Some fanfic writers may have made her his high school sweetheart. All we know, from "The Crossing," is that she apparently went diving in Tarpon Springs (where she thought it was getting dark) and snow sailing in New Zealand with her, and that he apparently enjoyed these activities enough to want to return to them as a wisp when he wasn't riding with Hopalong Cassidy.

From "Silent Enemy" we know that Natalie from Pensacola broke up with him via Dear John letter. This, mind you, is after he says four episodes earlier in "Breaking the Ice" that he's only been in three relationships and they all went bust, but I prefer to give him credit for already knowing the last one was bust. Otherwise me might have to conclude the writers just made up this shit without ever checking continuity.

From "Bounty" we also have this exchange about Tellarites:
ARCHER: Apparently they enjoy a good argument. It's considered a sport on their planet.
TUCKER: I've got an old girlfriend this guy might like to meet.

That's it. That's our total in scripture on Trip and girlfriends -- that I can recall anyway, and I have paid some attention to the matter.

Which means there's lots of room to play!

[Alelou]

Double post because I forgot Ruby. But oh man, do we really have to count Ruby? That was pathetic.

[Rigil Kent]

Double post because I forgot Ruby. But oh man, do we really have to count Ruby? That was pathetic.

Well, it could always be: Lisa (which in my corner of the 'verse was destined to fail since his eldest sister was also "Lisa"), Ruby, and then Natalie.

[Alelou]

Yeah, but that implies he actually thought he had a serious relationship with a waitress Malcolm ALSO nailed, and that's just too sad! But, I suppose it's possible.

I guess Lisa could be a sister. That does work, except you'd expect a sister who made that much of an impression on him to get mentioned at least once while he's mourning Lizzie.

[Aikiweezie]

I got the impression that the Ruby thing was nothing, just a flirtation.

Here's what I got from Star Trek.com

"Though he appears to be the charmer when it comes to the ladies, Trip claims that he has been involved in only three relationships, all of which ended badly. A long distance romance with Natalie from Pensacola didn't work out, and he regrets that he was unable to say good-bye in person. As a Starfleet trainee, he was infatuated with a waitress named Ruby at Mill Valley's 602 Club — the same Ruby that Lieutenant Reed once had a relationship with. Ruby had names all picked out for her children, and claimed that she would marry the first man who could guess them — Trip did his best, but was unsuccessful."

[Alelou]

TUCKER: I'm confident there'll be a Charles Tucker the fourth one day.
REED: Then maybe it's your wedding we should be planning. That's assuming we can find you a bride in the next day and a half. Any suggestions?
TUCKER: There was a little bar in Mill Valley where all the Starfleet trainees used to go.
REED: The 602 Club.
TUCKER: You know it?
REED: I was there more times than I can remember.
TUCKER: I met the girl of my dreams my first Friday night there. She was the one. There's no doubt about it. We had it all figured out. Where we'd live, how many kids we'd have. Ah, Ruby. Whatever happened to you?
REED: Ruby? You don't mean the waitress Ruby?
TUCKER: You knew Ruby?
REED: I knew her more times than I can remember.
TUCKER: Ouch.

Ouch indeed. Either Tucker was blowing air out his ass about Ruby -- my preferred theory -- or he seriously lost his heart to someone who apparently picked one officer each season, like Susan Sarandon's character in Bull Durham, or something.

[Aikiweezie]

I agree with your theory Alelou. In the flashback scene at the 602 in "First Flight" Ruby and Trip did not seem like a couple. Just a flirtatious thing. And given the fact that the 602 was so close to Starfleet she probably had a lot of young officers like Trip falling all over her, although Malcolm seems to have done a bit more than that. Or he was full of poop, too, but I don't think so.

[Aquarius]

I think the key is that Trip was "infatuated" with her. I don't think Ruby was a serious relationship.

Also, though he had three serous relationships, it doesn't mean he didn't date in between.

Natalie...well, it was a crappy way to break up, but in this day and age people do it by text message so why not. I always figured she told him she'd wait for him, then after he'd been gone for a while, reality sank in and she was like "screw this!" Not to vilify her or anything; it can't be easy sitting at home waiting for your sweetie to come home, especially knowing how dangerous his job/mission is and he might *not* be coming home. I also think that Trip had the best of intentions with her, but once he'd gotten out and seen the galaxy, opened his mind up a little bit, he might've slowly realized that Natalie wasn't "the one." Things might've been fine at first, but they were probably prime candidates to grow apart after a while.

[bluetiger]

Aquarius, I was waiting for my story to go up in Decon to answer this, but I think you are right. Trip could have dated women and not been serious. How sad would it be for Trip if he didn't have any fond memories of women he had been with. Surely the three that went bust were not all he experienced.

[Aikiweezie]

I think the key is that Trip was "infatuated" with her. I don't think Ruby was a serious relationship.

Also, though he had three serous relationships, it doesn't mean he didn't date in between.

Natalie...well, it was a crappy way to break up, but in this day and age people do it by text message so why not. I always figured she told him she'd wait for him, then after he'd been gone for a while, reality sank in and she was like "screw this!" Not to vilify her or anything; it can't be easy sitting at home waiting for your sweetie to come home, especially knowing how dangerous his job/mission is and he might *not* be coming home. I also think that Trip had the best of intentions with her, but once he'd gotten out and seen the galaxy, opened his mind up a little bit, he might've slowly realized that Natalie wasn't "the one." Things might've been fine at first, but they were probably prime candidates to grow apart after a while.

Or maybe not. I could see Trip as one of those guys who is a serial dater. Especially if he was in Starfleet and busy getting multiple degrees and promotions at such a young age. (I'm having deja vu )