Samara O'Shea, love columnist

Dear Samara, 

I lived with my boyfriend for three years and moved out last June. This is my first holiday alone ever. My family lives in New York and I live in Oregon. Work will prevent me from going home over the holidays. 

I have been invited to a few parties and I want to go so I don’t get totally depressed.  Since I haven’t dated for a while, can you give me some holiday dating tips?  I mean, are lonely people easier marks for guys who just want a fun time?  I am nervous about dating again, I hope I have not forgotten how, but I think I am ready. 


Dear Alone in Oregon,

I’m sorry this holiday season is difficult for you. The holidays can be a sad time—especially if a break-up took place during the year.

Despite the fact that being alone right now is surely devastating, I don’t think you should start dating yet. It doesn’t seem to me like you’re ready. The fact that you’re so scared of being taken advantage of tells me you have some insecurities that need to be faced. I recommend that you continue to be alone a little longer and try to make the most of it. Try to transition from being reluctantly alone to being purposefully alone. This will benefit you now and when you find yourself in a romantic relationship again.

Spiritual guru Eckhart Tolle says, “If you cannot be at ease with yourself when you are alone, you will seek a relationship to cover up your unease. You can be sure that the unease will reappear in some other form within the relationship and you will probably hold your partner responsible for it.” German psychoanalyst and author of the bestselling book The Art of Loving, Erich Fromm, echoes the same sentiment: “If I am attached to another person because I cannot stand on my own two feet, he or she may be a lifesaver, but the relationship is not one of love. Paradoxically, the ability to be alone is the condition for the ability to love.”

If you would like further explanation of how being alone is an asset to intimate relationships, I like what Dr. Suzanne Phillips has to say.  Here’s a sample: “True intimacy is possible when you have the ‘capacity to be alone’ because it implies choice. You don’t have to be with someone because you fear that being alone leaves you without stability or value.”

This is why I encourage you to try and enjoy your own company this holiday season. Of course, go to parties and have fun with your friends but also relish your alone time. If you enjoy cooking, then cook. If you don’t, order Chinese. Stay in your pjs all day and watch movies. Read books you’ve always wanted to read and write in your journal. If you don’t keep a journal, try. See if it does anything for you. Limit your time on social media. Photos of happy families on Facebook will make you feel worse. Pease keep in mind that they are only photos and not proof of actual happiness.

If you chose to go this route, I have two books I’d like to recommend. The first is my book about unrequited love. I normally don’t pimp my book out like this—I promise! But I think it applies to your situation. In the book I discuss ways to avoid being taken advantage of when dating as well as ways to bolster your self-esteem. Reinforced self-esteem is helpful when dating because there are inevitably guys who don’t call back when we really reallywant them to. It happens to us all!

I will also point you toward a book called Calling in the One. This is a workbook—a work-on-yourself book. There is one lesson every day for 49 days (seven weeks). This book prepares you for dating internally—by helping you face insecurities and forgive yourself for past mistakes—as opposed to externally—how to dress, what to say, where to go etc. The promise of the book “7 Weeks to Attract the Love of Your Life” is cheesy. But the advice and the writing is fantastic. Of course if you do end up meeting the love of your life in 7 weeks, no harm!

I suggest you start the New Year off with Calling in the One. Seven weeks into 2016, see how you feel. When you are no longer afraid of being taken advantage of and when you trust yourself to know that you will walk away from any person who isn’t treating you with respect, then you are ready to start dating again.



 You can ask Samara and Caroline questions for the Love & Life Advice Column here at

* The ideas and advice presented here are not a substitute for professional advice. Talk to your psychologist, counselor, physician or health care professional for situations that warrant further analysis.