Midlife Dating-Don’t Hold Yourself Back

Isn’t life funny? When you were 12, you argued with your parents to let you date.  Then, when you started the process, you found that the flirting was fun and so were some of the things you did.  However, the part of getting to know someone, the possible rejection, the disappointments, and the pains of love made you realize why your Momma told you not to rush it.  If and when you finally settled down, there was a part of you that was relieved at being out of the dating pool.  Now, fast forward a few years or a few decades. You are widowed, divorced, emerging from a long term relationship, or just sick of being alone.  You are older and ready to date.  You find that you, not your parents, are the one who is holding back from getting out there again to pursue midlife dating.

Why is that?  Dating can be hard work!  The world has changed.  Most significantly, you are a different person, with a history unthought of when you were 16.

The basics of midlife dating are the same.  You meet someone who appears to have similar interests and who is attractive to you.  In addition to the age-old way of meeting a potential date at school, work, church or a club, the internet is now a major way to hook up.  When you finally meet in person, you still have to determine if they are personable, compatible, and worthy of future contact.  As a midlife dater, your first face-to-face encounter is comparable to a job interview.

Let’s go there for a second. Even if you go to a job interview with impeccable credentials, even if you manage to get past nervousness to present the “real you” to the interviewer, there is still protocol to observe.  When you are asked to tell something about yourself, you don’t start from age 2, you hit the high points. You don’t dwell on past work experiences, especially bad ones with awful bosses.  You focus on how your work and personal skills will be of use to the new company.  As much as you need and want the job, you try not to appear desperate! You are sizing up the company as much as they are sizing you up.

The first dates that you have with a person put you in a similar situation.  Your goal is to reveal a little of yourself, learn about them, and in the process of conversation, find out what you have in common.  You aren’t trying to seal the deal on a life partnership – just figure out if you want to go to dinner with the person again.  Whether your past relationships were sensational, boring, antagonistic, loving, or somewhere in between, the first date is not time to offer your life history or dwell on the past.

Undoubtedly, whether your last mate was the love of your love taken by death or the scum of the earth who you divorced, you have strong feelings about the relationship that remain with you.  After the relationship ended, you took some time to process your feelings. By the time you get to the point of dating, you should have made peace with the past and given yourself permission to bury it!  You don’t want to make your past a third wheel at the dinner table!

As a mid-life dater, you are likely to consciously or unconsciously measure new dating partners against the standards set by past loves.  You might want to ask a lot of questions of the new person sitting across from you.  As natural as this seems, it is better to dwell on common interests than play 20 questions. A lot of what you want to know about someone will come out in later interactions.  There is plenty of time to fill in the blanks about what you want to know about them.

Just as the reward for a successful job interview can be a fulfilling, exciting job, midlife dating can open up a new chapter to your life.  By not dwelling on the past, you can enjoy yourself and build a new future for yourself.


  1. ron

    I enjoyed your article and agree that dating in midlife is a much different affair than when we were in our twenties. I share your view that the first date is not the time to “dwell on the past or offer up your life history”. Rather, it is a time for comfortable, mutual exploration. I always recommend wearing the hat of sincere “curiosity” and to limit the length of first dates to no more than a couple hours. Relationships take time to develop and the process can be both exciting and challenging. I have found some of the keys to mutually fulfilling dating are: respect, authenticity, transparency, honesty, and leaving yourself and your date to be in freedom to be who they are. I leave you with a favorite story:
    When a young man asked Gandhi to share about love, Gandhi paused and then replied…. “Respect …. Respect is the minimum expression of love”.
    Offered in support of Conscious Relationship,
    Ron Capocelli, CPCC

  2. Jo

    Liz, I spotted the intro to this on Twitter and, just wanted to say that, from experience, I so agree.

    It’s just too easy to divulge a whole load of stories that without knowing more about each other can lead to the hugest pile of assumptions – good and bad!

    Past history and the stories people choose to tell can be really informative, but they can also add a whole load of baggage that you just don’t need at the beginning of a relationship!

    I’m now with someone for whom the past is not the most important thing and it’s taken a while for me to get used to that. The great thing is I don’t constantly undermine myself by comparing myself to someone else’s history and instead really enjoy creating a shared story together. We’ve been together for a while now and it’s great!

    1. Liz

      Jo, many thanks. I am pleased you enjoyed my article. Creating a shared story is very important. Happy to hear about your successful relationship.


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