No Date on Valentine’s Day?

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DEAR MIDLIFE BACHELOR:  Just last month, my long-time girlfriend and I finally broke up. This was several years in the making, and going our separate ways was definitely the right thing to do. We still did our Christmas together with her family, we just didn’t pay too much attention to each other, and honestly I don’t think anyone even noticed that we weren’t interacting. I still love her but am not “in love” with her. I guess I’m ready to date, and have maybe a woman or two in mind that I want to ask out but it’s only been a few weeks since we officially broke up. And we still talk every other day or so.

Here’s my question. Valentine’s Day is coming up, and I’m not sure if I should do something with my ex, or if I should just not do anything at all. I have not been without a girlfriend (or wife) on Valentine’s Day in 10+ years. What do you suggest? What would you do?


MIDLIFE BACHELOR ANSWER:  First of all – you broke up with her, and just based on that alone, I would not plan anything with her for Valentine’s Day. You’d just be prolonging the agony of the breakup – assuming there is agony. I’m a big fan of putting one’s past behind them, and moving forward as quickly as possible … that way no more time or energy is wasted.Your next issue is – what to do on Valentine’s Day when you do not have a date?  Fortunately there is a really good and complete article right here on to help you.What to Do on Valentine’s Day when You Do Not Have a Date

Read the above article carefully – it contains the official lists of THINGS TO DO and also THINGS NOT TO DO on Valentine’s Day to preserve your integrity, and to avoid the appearance of being a loser.

Now it is time for you to at least start thinking about positioning yourself for a successful return to bachelorhood – which is exactly what is all about. I suggest you read these sections of this site in this order:

You should also consider joining our Midlife Forum here – as we have a lot of men and women in a situation at least somewhat similar to yours, and you might find trading opinions and lessons to be useful and entertaining. Good luck!

MARCH 6, 2010 UPDATE – my good friend, Jennifer Dawson of, created the following Valentine’s Day webisode. Check out how she spent her Valentine’s Day without a date (this is hhhot) …


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About the Author

Midlife Bachelor chronicles lifestyle, dating, and relationship experiences and advice to avoid a midlife crisis. Readers like you are often beyond young adulthood in their 30’s, 40’s, and 50’s that want to understand how dating, sex, relationships, and love fit in with our lifestyles.