Been dating a woman nearly twice my age for 4 months now. Not too long ago we planned a trip for early January to go scuba diving. Quite a bit of money from both of us is tied up in the trip. Since then I've finished my certification and am really excited to go. A few weeks ago I discovered a "Red-Flag". She was staying in her time share for a week and I went to stay the first weekend since I had to come back for work. I was very high when she was packing and I saw her put a condom in her bag (we don't use them). I told her to take it out since she wouldn't need it. Next morning I say, "I was pretty out of it last night, did you take the condom out?". She replied, "I think so", which I SHOULD HAVE called her out right then and there (she knew what she was saying). Later when we're at the destination I see it in a bag when I'm looking for floss....yet I didn't call her out (when I should have). Aside from that everything is smooth sailing.

A few days ago I ended up browsing Craigslist personals randomly and saw a W for M post. Now the stats (age, height, etc) were slightly off, but it sounded exactly like her. It's hard to describe but the tone, specific things she's said before, and little nuances made it seem like it WAS her. Ended up making a fake email and sent her a message and picture of guy with features I know she'd like, but never a response. I forgot the context, but when we were talking later I said jokingly, "Oh, does that mean you're going to trade me in for one of you CL bf's?" and laughed it off. The next day the post was removed.

I'm visiting family for a week soon and then the trip is just a few days later. I was thinking of saying family stuff came up and I can't go (I have the airline tickets and would get a refund, but take a bump on the hotel). IF she cares about me at all she will still be upset, but end up understanding and want to reschedule. IF NOT, then she isn't someone I'd want to be with anyway.

I'm not sure If I should drop her now, try the above method (to weed her out), or just go on the trip...because frankly I've been training for it and still really want to go (but run the risk of a bad time....which has happened on a trip to me in the past).

You won't get a good answer here.

There are too many intricacies in your relationship that no one is privy to, thereby making any response completely irrelevant.

My gut tells me to run as fast as you can, but again that's only on the limited information I have.

astute observation oceanx. I have a choice to make.

1.The sick part of wants to check out mentally, still go on the trip (to have fun), and use our remaining time together to experiment (playing with my behavior, attitude, etc. to see what kind of response is elicited).

2.Tell her family matters came up and I can't go. Gauge her reaction.

Personally I don't know why you bother with a woman twice your age, but if that's your thing, whatever.

She clearly was thinking to get some side dicks.

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Exclusive?

Yes, exclusive. I'm mid twenties returning to university after long while. I've had ton of fun getting with the college age girls since being back. Really nice to look at and feel but couldn't stand their personalities to do it anymore. That's why I decided to go much older (hopes of having their shit together).
*update*
Told her I couldn't go on trip and she tried everything under the sun to change my mind and said she was still going. After I got home she called me, apologized, and said she will work on getting a refund.

Maybe meet better quality girls? Plenty of 20 somethings that got their shit together.

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My in depth texting & dating guide.
There's no such thing as shit-tests.
How to keep a girl.

why not just call her out?

I dunno...something is iffy here.... Why are you browsing CL personals? Also, you don't go from 20 yr olds to 50+ year olds like that because college chicks are immature. This thread is off and I suspect you're leaving a lot out.

I'll say this though, you are what you attract. If you wanted more mature chicks, DONT ACT LIKE AN IMMATURE CHICK. From the moment you saw that condom you shouldve manned up and called it out. And not done the whole CL fake profile shit. Now you're making up family matters instead of calling out shit. Thats what boys do. I'm just saying this to say, get your shit together as well.

Both of these.

You were cruising Craigs for a back up plan already.

Why worried in the 1st place? She's x2 her face is on schedule to melt off soon anyway.

Fuck her while the fucking is good, go on a fun filled vaca, and drill all her orifices.

Look for more when your done.

This isn't a Dear Abby, "I fell in love with a cougar." heartbreak forum, it's a pick up forum.

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As I mentioned in the original post, I Knew I should have called her out immediately but failed to take action. I'll bring it up when I see her at the end of the week. If I end up going I'll have a great time and not set any expectations.

I'm sorry I just find this situation funny

1. You're with a 50+ year old chick in your mid twenties. How you go from tight smooth skinned college chicks to wrinkles and varicose veins is just crazy. And like you seriously dated this woman like there was a future

2. It's funny when I picture this 50+ yr old woman going out looking for dick like a chick on spring break. Like you're the YOUNG guy, but SHE's the one preparing for sex.

3. Craigslist...who the hell uses cl to get laid nowadays?! You might as well have said she had a Myspace up looking for guys. And its funny you were even on there too. Pof, Tinder, Okc...come on people its 2015

4. Then you're on craigslist, to send fake messages to catch a 50 YEAR OLD WOMAN. You're the YOUNG GUY half her age, yet you have to be tracking her and suspicious of her. Condom should have been the end. Heck, the age should have been the end and you shouldve just kept it as fuck buddies

Seriously though, I hope you can laugh at the situation.

Tbh, if she was cheating or open to it, thats messed up...but I gotta take her side if she was open to new dicks. SHE'S 50 YEARS OLD. YOU'RE 25 ISH. She'd be stupid and crazy to have a serious committed relationship with you. She should be looking for other options. As should you have. And judging from how you actually took her seriously, couldnt and havent been able to call her out, went through effort to find out if she was cheating...I'm sorry, I can't assume that you have options and didnt possibly pressure this into a relationship. You cant tell me a young guy who was banging 20 year olds, goes with a 60 year old, and cant call out when he catches her doing something. Thats like telling me you had a 100k job and was a boss, went to a 40k job, and then somehow you're afraid to lose the 40k job and will do all kinds of shit to keep it. Most likely you're the needy one in this. And that's funny, but truly sad that its like that.

Hahahah. So true.

_________________
I know my place. It's me on top of the world.

My in depth texting & dating guide.
There's no such thing as shit-tests.
How to keep a girl.

Hope I'm not double posting. I thought I made a comment on this tthread but obviously not.

The fact that you seem more interested in "experimenting" and trying to get a rise out of her while on vacation than actually doing something more valuable with your vacation time says a lot about you and your relationship. And none of it good.

If it was me I would enjoy the fuck out of my vacation, and then look for options when I get back.

And why the FUCK are you with a woman who is twice your age? There is literally no reason I would be with a woman twice my age unless she was filthy rich and I already had kids. Yeah that sounds like me being a goldigger but....that's the only way it would happen.