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Pickup Coaching
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Joined: 11/17/2017

This is the first time I’ve ever been in this position but I’m in a dilemma of choosing between two beautiful women. These two women, Elena and Isabela, who I’m fortunate enough to meet and get to know are as different as night and day.

The first woman, Elena is 28 years old, she’s a banker and is outdoorsy because she likes parasailing, sports and trekking. At first, I was a little bit intimidated because I’m a bit out of shape so I couldn’t come up with some first date ideas. She took pity on me and suggested that we have dinner instead which was fine. I was thinking about what I need in my life and she fit that mold because she’s active and young and knows how to have fun.

I’m not sure why this young Latina woman was so into me but she was. She told me I’m mature and set in my ways, and that she needed “taming” so she could get her life together. In my opinion, I think she’s handling her life alright.

The second woman, Isabel is 32 years old. She’s a single mother of an adorable 3-year-old and near my age, although there is a 10-year gap. When I met her, she had this quality that I really liked and instantly made me think of “wife.” I can see that she loves her son and it’s refreshing to see as my kids have all grown up. I’ve also bonded with the little guy and I would really love to spoil him someday and play basketball when he’s a bit older or whatever he likes.

To give a bit of background, I’m a 42 divorced male with 2 college-age kids. I’m from Orange County and I live comfortably with a modest job that I love. It has been a while for me since I’ve had a girlfriend so I decided to date again after 4 years of being single.

I met these two women when I went on a tour in Colombia.

Now, my dilemma. I like these two women. I need to be practical. Elena and Isabel were on the tour too because they were in the same boat as me. They both have expressed their interest in me as we’ve gone on to a couple of dates. Is it weird to say that I equally like them both? Any advice you can give? Thanks in advance.

Joined: 01/18/2012
Fuck them both, homey. 

Fuck them both, homey. 


I go in and I'm crisp, clean and my vocals are fucking coming out like music. - Anonymous MW student

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Meow's picture
Joined: 03/27/2013
Here is my general rule of

Here is my general rule of thumb nowadays... you don't worry about this type of stuff until sex goes down lol. Good sex is important, you deserve to be satisfied with someone that really turns you on, no shame in seeing both of them and making your decision later on.

Joined: 10/15/2012
Bang both of them. Get

Bang both of them. Get serious with one later on if that’s what you want.


Big Cat