Starting over is one of the scariest things I have to do. I haven’t dated since college and I’m 52. I just don’t know where to begin. Am I too old to date? I’m not sure I’m even ready – It’s only been 6 months since my divorce and I still think about the affair. How will I ever trust again?

That’s how Mark began our session. Mark is not alone with his anxiety about starting over. Most people who find themselves divorced after years of marriage feel it’s daunting to think about dating again.

Yet they do. We are not meant to be alone. I admire clients taking the huge step of looking for a partner at midlife and beyond.

photo relationships work newly single first date

Once married, most people never expect to have to date again. It’s anxiety provoking to put yourself out there, especially if you’ve been hurt by your ex-partner or if it wasn’t your idea to end your former marriage. Starting again takes guts.

People worry about where to meet other single people, how to act on a date, how much to reveal, what to talk about. Many have never done “online dating” before. Creating a profile and searching online for potential mates can be overwhelming, frustrating and time-intensive. But still, most people don’t want to be alone.

Here are 5 keys to help you start dating again:

1. Let yourself be vulnerable.
Meeting someone new and heading into a relationship requires you to be vulnerable. That is especially hard when you’ve been hurt. When you open your heart, you may find yourself feeling the pain of the former relationship, since it’s scary to open up again. Do it anyway. You’re more resilient than you think.

New beginnings are often disguised as painful endings.
– Lao Tzu

2. Stay positive about starting a new chapter.
There may be times when you get anxious or frustrated and stop trying. Give yourself a break and then start again. Persevere. Second time around can be even better.

You are never too old to set another goal or to dream a new dream.
– C.S. Lewis

3. Be mindful about what you want in a partner and establish your deal breakers.
Lead with your head more than your heart. Think through what qualities you want in a mate – “must haves,” “would likes,” and “deal breakers.” After each date think through what you learned about the other person. Don’t minimize things that concern you. Idealizing a new partner can get you into trouble. Keep your head and your heart on earth.

One of the best times for figuring out who you are and what you really want out of life?
Right after a break-up.

– Mandy Hale

4. Use what you learned in your previous relationship to avoid the same mistakes.
We tend to repeat patterns in relationships. Be aware of your behavior and responses to not repeat. And be wary of holding your new partner responsible for your ex-partner’s hurts. Leave your old baggage behind as you start down a new path.

Do not sabotage your new relationship with your last relationship’s poison.
– Steve Marabo

5. Be authentic from the start.
We teach people how to treat us in the beginning. If there’s something that bothers you, be assertive. Speak up. Use “I” statements to address concerns; don’t sweep them under the rug. Be true to yourself and ask for what you need.

The beginning is the most important part of the work.
– Plato

Lastly, don’t forget, as you meet new people and do this work, to have fun. Enjoy and appreciate the new experiences you will have.

No matter how hard the past is, you can always begin again.
– Buddha

If you are in a relationship and wanting a fresh start, or are looking for a fresh start in a new relationship, Bob and I can help. Call us at 410-363-2825 or email

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