Lifestyle Sharing the Struggle

Sharing the Struggle: Awkward First Date Conversations

Hello again Shuffle readers!


I had drinks last week with a man I met on Bumble.  He is 31, I am 29.  We hadn’t even received our appetizers before he blurted out he had been married before and he never wants kids.  As a general rule, I don’t talk about kids or past relationships on the first date, so I was a little blindsided.  I want children. It’s something I’ve always wanted.  I sat through the rest of the date, knowing it was never going to work and resenting him for putting me in that position so early in the evening.  What should I have done in that situation and what should I do now that he is asking for a second date?

Helplessly Seeking in San Antonio


I have been where you are and the answer is one that I bet you knew already. Honesty is the best policy.

Women have been socialized to pacify men and protect their feelings. We do it all the time. We smile and change the subject when a coworker makes an inappropriate comment. Women are also known to “fake it” from time to time. Which essentially means that we weren’t satisfied by the experience, but rather than say that we avoid the confrontation completely and forgo pleasure that is rightfully ours. This has to stop. In this situation, he put his cards on the table and you should have done the same.

Every serial dater knows there are certain things you just don’t talk about on a first date. Kids, marriage, religion, money, and politics. Just save it. These topics should be considered off limits until after date number two.

At 31, he is not going to change his mind. Even if it’s possible he would, you shouldn’t count on it. Take him at his word. In this case, I would have stated that I do want kids. No need to give timelines or the names of the pre-schools you have picked out, but let him know the two of you are on different pages.

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Be honest with him and tell him that a second date wouldn’t be best for either of you and explain why. His reaction matters less than the lesson he must learn. You could be the catalyst that turns his dating life around. In Girl Scouts we were taught to leave a place better than we found it. So, leave him better than you found him. If you think he would make a great friend, make an honest effort to be his friend. Otherwise, you can part ways knowing that you stood up for what you want.

If you were looking for a quick exit, suggest meeting for coffee or a drink to keep things short and sweet.

Have a question for June? Submit your questions or stories to or tweet us @Shuffleonline!

About June

June was born and raised in the south where “bless your heart” is an insult. Self professed serial dater and an expert in all matters of the heart. June also enjoys volunteering, dancing and sewing.

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