Should I Reveal This On A First Date?

I want to hear the relationship/dating problems that are stressing you out. Tell me what’s on your mind. Submit your own question here. You can also email [email protected].



I am concerned that my romantic life seems to have stalled, and I have little optimism. I am a 39-year-old man. My recent dates with women have not resulted in a second one. Some dates have gone OK, in my opinion. I liked some of the people, others did not fancy me. I still had fun. However, I seem to have terrible luck … or am I somehow repelling people? My recent life-altering history seems a part of this issue.

Four years ago, I suffered a traumatic brain injury on the job. I was recovering well – until two months later when I had life-saving brain surgery. My life became a powerful tornado. I could not drive, I had little strength, could not read for a time, and I was emotionally fragile. I also had cognition issues. That’s just a sample of the challenges.

Now I am doing relatively well and I have tempered my challenges. As a result of the injury, I have not had physical or emotional intimacy in a long time. My question is: Why am I having such bad luck or results in my dating life? Sometimes I tell my date I have a TBI because I otherwise feel like I am hiding something that could be a problem in the future. I know that usually ends any chances for a second date. I feel emotionally and physical lonely, and it is degrading my otherwise good mental health.

– Lonely with no hope


Please know that many first dates do not lead to second dates. A good portion of this column is people wondering why a nice connection didn’t lead to more.

It’s frustrating but typical. The process can be exhausting – which is why I have a “dating fatigue” category for Love Letters.

You bring up disclosure and honesty on first dates. My take: I’m not sure these early outings are designed for monumental sharing. Some people don’t mention their divorce during a first date. I’m not sure chronic illnesses come up during a one-hour coffee.

I’m not suggesting you hide information, but I do think you should give yourself some time to decide if someone has earned your attention and trust. Ask questions and listen. Have fun. If you spend 10 minutes explaining what you’ve been through, you’re not as present for everything else. It’s OK to wait.

One of the lovely things about being 39 is that many of your peers have more experience with everything. Some are divorced and feel like they’re dating for the first time in years. Others are more appreciative of good company than they would have been at 25. Also, people around forty (and older) might be used to health conversations. Maybe they know more. Now that I’m in my 40s, more of my friends have experienced the medical system. They’ve done caretaking for children or parents, and they’re less likely to assume that everyone’s in perfect health.

Have patience. Lean on friends for support. Balance first dates with activities that feel rewarding no matter what. For every first date that could go nowhere, see someone who plans to be in your life forever.

– Meredith

Readers? What are first dates for? How often do they lead to second dates? Pep talk for optimism?

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