Dating at Midlife/Unsure what happened


QUESTION: I was introduced to a guy about a month ago and he really hit it off, it seemed. Spent most of our time together with other friends. However, one night both us had a little too much to drink and ended up kissing. The next day he called off our "date" for that evening saying he was backing off because he felt like he was moving into a relationship and he was not ready for that after being badly hurt not long ago. He wanted to be friends. Although very disappointed, I decided I would try being the pal he wanted and we had some contact most every day thereafter. I had apologized to him for crossing the friendship line because he said I was the one who kissed him first. I told him I promised to never let my lips come near his again and would be his friend! Today, he sent a text asking when we were going to play cards again and have a drink. I am sure not just the two of us. I sent back "No more drinking with you!!! Cards whenever". He sent back "Fine" followed by "Sorry you feel that way". What??? I sent "No one said you can't drink so no need to pout. Remember the affect it has on me so not a good idea. LOL" I don't understand! He was the one who seemed to have a problem with kissing me. I, however, am very attracted to him and would potentially like to be more than friends, so I need to keep a clear head if we are going to spend time together. I am not sure what to do at this point. I never dreamt it would make him mad. I look forward to your response. Thank you.

ANSWER: Hi Renee, I'm sorry things turned out the way it did, since you're attracted to him. I don't know what would prompt his "I'm sorry you feel that way" about not drinking when you're around him. Maybe he would feel awkward if everyone else is drinking and you're not?  Maybe he  just wants you as a friend and doesn't want you to do something that you normally wouldn't do, when you hang out, like drink with friends. He may be feeling guilty or responsible that you won't drink in front of him, because he knows you are attracted to him.. It's a good idea to stay away from him until you are sure you can be yourself around him. I don't think he is mad at you. I think he's confused. On one hand you're saying you want to be friends and on the other hand you're saying I can't drink and be myself around you. Decide whether you can truly be a friend or not. Best of luck with your decision  

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QUESTION: Thank you. Our mutual friend, Mary, has known him for 20 years, worked with him and is married, yet he wants me to be the same type of friend. I thought I would give it a shot but just don't think I can do. I being around him would always make me desire more and require me to pretend otherwise. I thought he might understand this.

I think it would be much better if you look for someone who is emotionally available. Don't be surprised if you back off from wanting a relationship with him, he suddenly tries to attract you back. Men have very fractured egos and have a lot of trouble with rejection. There are plenty of good guys out there. Good Luck!

Dating at Midlife

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Lauren Stevens


I can answer all questions pertaining to dating, dating at 50+, online dating, health and sexual issues regarding relationships.


I have been a life coach and all expert coach for over 15 years.

I have founded and facilitated Life After Divorce a coaching program that promotes and enables life changing events. I also facilitated Transitions a support group for the traumatic experience of people going through divorce and the newly divorced.

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