Her previous bf was abusive and extremely controlling. I've been careful helping her deal with the past abuse and avoiding any appearance of being controlling.
Due to the bf she lost custody of her 2 children, now 13 and 17. She's spent a lot of time the past 15 months in her hometown (a 5 hour drive) trying to regain custody. I've been paying her large expenses and haven't taken a true vacation in over three years.
She tells me 2 weeks ago she's taking a 5-day trip to Las Vegas for a "bridal shower" for an old friend. I initially did not say much, not wanting to come across as "controlling".
- I don't know the bride or any others on this trip. I do know friends from her hometown have unsavory pasts and my gf managed to get in some serious legal trouble with them in her early 20s.
- My gf is expecting me to pick up her costs for a nice room at the Palms, and all her other expenses for the trip. By staying 5 days, costs will end up being 2-3 times more expensive than if they'd just paid slightly higher air fares for a weekend.
- The 5-day "bridal shower" sounds sketchy. Most bridal showers I've known involved a restaurant or someone's house for a few hours to open gifts and some "adult" party favors, not 5 days in Vegas.
- She used to work as a stripper, including one stint in Vegas. For several years she definitely fit the stereotype- hard partying, with alcohol, sex and drugs thrown into the mix. A number of her hometown friends were part of her sex industry and hard partying days. The mixture of old friends, alcohol and her old stomping grounds, along with her lack of candor, just seems like a lit match looking for a can of gasoline.
Is the problematic handwriting already on the wall in bold print or am I overreacting?
One thought was to tell her I'll only fund the trip if I can with her. If I was on the trip I'd be ok stepping aside on occasion for her to spend some girls only time either at a dinner or maybe even a show or a little dancing. But 5 days of this 24/7, on my dime seems way over the line. Is this a legitimate option to present or is it destined to label me a "control freak" with trust issues?

Trust your instincts. I know you don't want to, because the implications may mean that she may not be your Ms. Right, and there may be an uncomfortable conflict brewing if you say no to her, but you're 100% correct in thinking that you shouldn't automatically be paying for a five day "bridal shower" in Vegas, given your concerns about her past. Typically, a bridal shower is an afternoon lunch or tea. Not a 5 day ordeal in Vegas. A bachelorette party may be a night or a weekend in Vegas -- but rarely is it five days because most people don't have that kind of free time. In addition, if it was legit, there would be a wedding invitation, to which she'd be asking your to be her plus one guest. So, it sounds like this is more of a wild vacation with friends, than anything else. And since you have problems with her past behavior with these friends from her past, it's time for a conversation with her about relationship boundaries and expectations.

Second, be careful not to enable her. She may have had a controlling and abusive boyfriend in the past, but that doesn't mean you're one, too! You get to have your boundaries and say no when you feel things are crossing lines for you, without being labeled controlling. If you don't, then the control issue remains in your relationship -- only you're being controlled by her.

Third, if you've usually pay for her vacations, let her know why you don't want to pay for this one. If you don't usually pay for her vacations, then talk with her about why she expects you to foot this bill. Don't get angry. And, do approach the topic rationally and use it to talk about who pays for what in other areas, too.

Lastly, it sounds like this isn't about money. It's about her character -- and that's a big one. If she's lost custody of her kids because of her past choices, she may lose a good relationship with you through similar choices... not saying she definitely will, but it's something you have to look out for. Keep your eyes open, don't get angry, but do address these issues with her, so you're both clear on what's going on and what's okay with each of you, as well as what's not.