Don’t give up on dating after setback

Dear Annie: I recently dated a woman for five months. She is in her late 70s like me. She is twice widowed. Husband No. 2 passed away three years ago. My lady friend and I were together for dinners, outdoor community events and theatre performances, and I competed some light landscaping work around her house and some minor household repairs. On my very first date with her, I told her at dinner that I am a social cripple when it comes to dating. I hadn’t dated anyone in years. I was also concerned that she might be still grieving for husband No. 2. We had a total of 36 dates together. About halfway through this dating saga, I asked her whether I was doing OK. She replied that I was doing fine. However, soon after that, when I asked her to attend some club picnics and a family birthday party, she declined, citing conflicts. I sensed that something was going wrong. On the 34th date, I asked for a hug. This was our first physical contact. While I hugged her, she held her hands to the sides of her body and looked at the floor. It was a very brief hug. She repeated this stance on our 35th date. On what would turn out to be our last date, she loosely placed her hands around my waist and looked down to the floor, and this hug was also very brief. I left the house with hurt feelings, knowing something was going wrong in the relationship. The next day, I got an email from her. (She emailed every day during our five-month dating adventure.) She stated that she did not want to become “emotionally involved” and that I should find another lady. I emailed her a brief reply, ending our relationship on a cordial note. However, I am upset. Why did it take her so long, five months and 36 dates, to tell me about her emotional feelings? I did not discuss our relationship progress because I was concerned about her grieving condition. The relationship is over. I would just like your comments and observations on what may have gone wrong with her and me. —Senior Dating Adventures

Dear Senior Dating Adventures: The digital Dear John was a low blow. Good manners and basic human decency dictate that breakups should happen in person (except, of course, in cases in which one partner feels unsafe around the other, which was not the case here). At the very least, she could have picked up the phone to call you. That said, rather than focus on what she did wrong, we should focus on what you can learn from this experience. It sounds as though you need to work on your confidence. It’s OK to mention early in a relationship that you’re rusty at dating; that’s authentic, and people appreciate authenticity. But bringing that up often and seeking reassurance that you’re doing OK — that sort of insecurity can push potential partners away. Sometimes a “fake it till you make it” approach is best. Act confident and the feeling will eventually follow. Also, the fact that you counted dates suggests you may have been fixating a bit too intently on the relationship. Next time, don’t lose sight of your friends and your own hobbies. Give new flames some room to breathe and grow. Lastly, don’t give up on dating altogether. No adventure is without its setbacks. Adjust course, and forge ahead.