This Woman Needs Dating Advice! Should She Go To Vail For New Year’s?

By Jackie Pilossoph, Creator and Editor-in-chief, Divorced Girl Smiling site, podcast and app, Love Essentially columnist and author

Here is an email from a divorced woman seeking dating advice. Read my advice and then give her your opinion!

 I’ve been dating this guy for 2 years, who is really “NICE” would do anything for me…trips, gifts, and sex is good. BUT I don’t feel he is my sole mate! I’m 44 , he’s 57 , he has an 11 year old son and mine are in college.

I just feel like there is someone else out there for me. I don’t want to make the same mistake again. Although he’s not like my first husband I just don’t feel the butterflies. I tried to break it off for a month telling him I needed time to continue to find myself ( and I didn’t even miss him) and now he wants to fly me to Vail for New Years eve.

I know you probably think I’m crazy not to want to stay with him but it has to have a warm fuzzy feeling all over for both parties, don’t you agree.?   He would love to spend the rest of his life with me. I don’t think I’m quite ready for that (with him at least)

 Recently I got re-acquainted with a high school buddy who is going through a divorce. He is 45 dating someone I think 29. We were like best friends in high school – he would have a girlfriend (cheerleader) but we would still go to lunch and dinners and talk about life stuff.  We then went off to college and reconnected at our 20 year class reunion .  I was just going thru my divorce and he was married.  We stayed in touch and an occasional lunch.

Now, since is separated, we have been going to dinners and having great conversations.  I have been there for him – advice tips etc.  He still is dating the 29 year old..not sure he is in LOVE with her but he says he thinks he might be.  He even met me for dinner with my kids and mom on Christmas Eve.  He’s adorable, smart, wealthy, polite, funny and interesting. I feel so proud being next to his side being at dinner and introducing him to my friends. He says I should go to Vail with my boyfriend. What would you do? 

I told my boyfriend I didn’t think he was the one for me but he continues to stick around. We do have a GREAT time when we are together. Should I just keep it going with OPEN communication or break it off completely because I think I know I wouldn’t want to spend the rest of my life with him? Would you go to Vail for New Years?? 

There could be readers who after reading your first paragraph are rolling their eyes and judging you. “Poor woman…deciding if she should be flown out to Vail by a guy who loves her??” BUT, I don’t see it that way at all. In fact, I have a lot of respect for you for not immediately agreeing to go on the trip just for the sake of a free vacation at a 5 star resort.

I think you are wise for thinking through your feelings and having the guts to admit that it might not be right. Do you know how many women would jump into a second marriage for financial comfort?? Furthermore, the fact that you have been honest with this guy is commendable. Truly. You must really like yourself for that. It takes guts and the risk of losing him.

Now, let’s talk about your high school friend. I have to say right off the bat, I’m not a fan. Sorry. It started off in high school. You were “his friend” and no more. He chose to date cheerleaders. He didn’t choose you. He again isn’t choosing you, as he is choosing the 29 year old.

I know I sound harsh, but remember that I am on YOUR side. I am giving YOU advice to help YOU, and this guy doesn’t sound like he is very good for your self-esteem. Your boyfriend is bending over backwards for you. He truly loves you. He will do anything for you. That doesn’t mean you should dive into a marriage with him, or even stay with him. Just recognize the difference in the way these two men feel about you. Love is hard enough, but is made easier when the guy really really wants it. “Marry someone who loves you more than you love him,” my mom always told me. I did not listen the first time around.

High school guy wants the benefit of your friendship, but he doesn’t love you in a romantic way. I’m sorry to say that, and I feel terrible, but that’s how I feel. How good can that be for your self-esteem? Fanaticizing that high school guy is going to all of a sudden realize he is in love with you and break up with his girlfriend? He never did that in high school and he won’t do it now. The only thing you might want to do is ask the high school guy if he would be open to dating you. Then you will know for sure. Then again, like the book and movie, “He’s just not that into you,” I’m a believer that if he wanted you, he’d make a move.

The bottom line is, neither guy sounds really right for you. I know it seems scary to be alone, but you don’t have to be. I think it’s wise to live day by day and do what you want to do. BUT, continue to be honest and upfront with your boyfriend. Go to Vail if you feel like it, and just have fun. Don’t rule out the boyfriend, but don’t commit to marriage either.

As far as the high school friend, maybe cool it off a little bit. Don’t be so available to be his therapist. Let him make the effort to see you and let him miss you. I’m not a fan of games, so I’m not saying play a game. I’m just saying, put your energy into meeting new people (both men and women) as friends and just be social. Don’t pass up any opportunities with anyone else.

Good luck and keep me updated! Happy New Year!


Buy novels by Jackie Pilossoph
Take the quiz to get recommendations Divorced Girl Smiling Trusted Partners

Sign up for the Divorced Girl Smiling newsletter to get weekly articles on divorce and dating.

Sign up
Listen to the Divorced Girl Smiling podcast! a weekly show about divorce and dating Download the Divorced Girl Smiling mobile app


Tracy Coenen - The Divorce Money Guide
Jerfita Compass Team since 2004
Divorced Girl Smiling welcome video
Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorced Girl Smiling is here to empower, connect and inspire you. Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling, the site, the podcast and the app. A former television journalist and newspaper features reporter, Pilossoph is also the author of four novels and the writer of her weekly relationship column, Love Essentially. Pilossoph holds a Masters degree in journalism and lives in Chicago with her two teenagers. The author of the novels, Divorced Girl Smiling and Free Gift With Purchase, Pilossoph also writes the weekly dating and relationships advice column, “Love Essentially”, published in the Chicago Tribune Pioneer Press and the Chicago Tribune online. Additionally, she is a Huffington Post contributor. Pilossoph holds a Masters degree in journalism from Boston University.

2 Responses to “This Woman Needs Dating Advice! Should She Go To Vail For New Year’s?”

  1. Kristen

    I agree with Jackie wholeheartedly! As I read your inquiry I noticed how you truly are seeking something more sacred, a connection that gives you butterflies and and an avenue that builds a two way street. Many women are swept off their feet by money and although the gentleman who wants to literally “buy” your affection, albeit, you know he isn’t your soul mate! Listen to your intuition and don’t settle for second or even third best. In essence you know what is best for you, in your heart, at this time. New Year’s Eve will come and go, the sun will set and rise again, but the feeling within, now that is what I try to focus on and in my opinion, so should you. Blessings to you on whatever your decision may be. May you walk into this New Year with an open, yet peaceful heart!


Leave a Reply

Your email address will not be published. Required fields are marked *