Guest post: Ian Oliver on dating after divorce, relationships and the holidays

In addition to being an unofficial Divorce Doula dispensing advice and offering resources for The Afterwife, I am also a bit of a Dating Doula I have been on literally dozens (maybe hundreds? I should check my spreadsheet) of dates; some good, some great, some never again. Does that qualify me as an expert? Probably not, but I have also helped many friends write their on-line dating profiles and vet on-line suitability of suitors, poured wine before AND after first dates and watched flirtation and fascination turn into love in the second act. I think a lot of people are apprehensive about dating after divorce and understandably so. Being married and out of “the game” for several decades, many of us find dating after divorce daunting or downright terrifying. Many of us have been traumatized by divorce: feeling rejected, navigating bitter battles with the ex, a feeling of failure, a fear of being unloveable. It takes a strong sense of self to allow yourself to be vulnerable with another person and many people are unprepared or unwilling to do so after their divorce. We throw ourselves into raising our kids or our career and say “If it’s meant to be, it will happen” but I believe that dating, like marriage (and divorce, for that matter) takes work.  You have to put yourself out there if you truly want a relationship and that takes courage, honesty and good advice.

I considered writing a book on this subject but was thrilled to receive a copy of Ian Oliver’s book “Getting Back on Top: The Uncensored Guide to Sex, Dating and Relationships After Divorce” because it is similar to the type of book that I would write. Ian is a financial advisor and relationship coach, Huffington Post contributor and passionate advocate for children-related charities and causes. His book is the perfect guide to dating after divorce and covers everything from dating sites to matchmakers, texting protocol, phone sex and The Ten Commandment of Sex, Dating and Relationships (“Thou Shalt Not Fake an Orgasm. Divorce Doula: Amen).  It’s a no nonsense guide to getting your mojo back after divorce and I asked Ian to guest post for me on the matter of dating over the holidays. I hope that you enjoy Ian’s post and it helps you navigate your way through dating after divorce. Please consider buying Ian’s #1 Amazon Bestselling book as 100% of the profits will go to children’s charities such as Promises2Kids, Voices for Children and the San Diego Children’s Museum. Sound advice,  solid philanthropy and he loves his mom. Ian is one of the good ones.

Dating and relationships during the holidays by Ian Oliver

Dating and relationships, especially after a divorce, are always hard but it can be even harder during the holidays. There are constant reminders, especially through media, of what a beautiful time it is to be happy and in love. Ads of happy couples and families are abundant and it tends to be a reminder of what could have been or even make you anxious of what the future holds. It can be a harder time for us singles…not to worry! In this article and in my book Getting Back On Top: The Uncensored Guide to Sex, Dating, and Relationships After Divorce, I point out the ways and give tips to make it better and to understand the reality of things.

So first of all, let’s remember that the ads and pictures out there do not represent reality. Most marriages end in divorce and for the ones that don’t, many are not as happy as those ads make them out to be. Ads do what they are meant to do and that is sell people’s dreams not realities.

Second, dating during the holidays can be fun, you just have to put yourself out there. As always, use the 4 main sources to find potential dates: friends (everyone knows a few singles), online sites like Match, E Harmony, Christian Mingle, J Date, or whatever your preference (Divorce Doula: I’m a fan of OKCupid. High geek factor & less bottom fishing than on Plenty of Fish) and also consider signing up for dating services and matchmakers. Many people are looking for exactly what you are during the holidays, but you will never find them unless you make yourself available. It’s like wanting a perfect body but never setting foot in a gym or never eating healthy. Nothing happens without a bit of effort.

Third, holidays are full of places to meet new people. Head out to a few holiday parties and fundraisers. There usually are many single people at these events and they tend to be more socially conscious and philanthropically oriented—both attractive qualities. If you have a few in one evening, spend a little time at each and evaluate the crowd!

Fourth, this is one of my biggest recommendations that people just can’t seem to grasp, and that is that if you see someone attractive at one of these parties or anywhere for that matter, go up to them and ask them out. Get into the holiday spirit and spread the cheer! A smile at a person will go a long way and tend to open doors to conversation. Don’t be shy, the holidays are perfect for starting up conversations about holiday shopping, the ambience, waiting in line, grocery shopping for holiday dinners, that funny Santa Claus in the mall, etc. There are a myriad of opportunities to strike up conversation. Don’t let one slip by. It will feel good to do it and you will be surprised by how many are interested and say yes. And if any don’t say yes, just know that as long as you were polite and genuine, they were probably flattered and you might have just made their day.

When you do land that date the holidays make it easy to have amazing dates. Take the things you like to do always hiking, a walk on the beach, hanging out at a cool coffee shop and trying their new holiday coffees or teas, and do it with the person you are dating. It will give them an idea of what you like to do.

Many people think that dating around the holidays can be a bit tricky, but it is probably easier than any other time of the year! You have an excuse to give someone a little something that shows them you care without being too forward. You have an excuse to invite someone to holiday parties with your friends (and if they seem uncomfortable can leave whenever you want rather than at a sit down dinner). You can even show them that extra bit of affection under the mistletoe. It’s the holidays!

Just be open to meeting people anywhere and everywhere, if there is someone already in your life be extra kind to that special someone; and in the process of it all appreciate your freedom, your choice and your independence. Be present and realize how lucky you are.



About Pamela

I’m a Vancouver-based divorced mother of two awesome boys embarking on a respectful, amicable and often humorous co-parenting adventure with their father. By day, I'm a publicist for good causes + companies at
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