6 Dating Questions From the last week


Sometimes I think I’ve heard every imaginable dating question with my dating consulting service. Then I hear a new one! Helping singles navigate online dating for over 25+ years, every now and then and I pause before responding.

These are questions from both my existing clients and singles who call me who are struggling with online dating:

1. Michael, a 44-year-old architect asked me this: I’ve been on 3 dates with one woman but there’s no spark, no attraction on my part. Should I keep trying and see if I suddenly feel physical chemistry?

 As he asked me this, and knowing him fairly well, I read between the lines and knew she felt the spark, but he did not. My general rule of thumb is that if you don’t feel attraction by date #3, it probably won’t happen. Yes, it does sometimes happen on date #1, but I have just as often seen it occur on dates 2 and 3. After that, no. And Michael wasn’t looking for more friends. The kindest action is to move on!

2. Do all women online want marriage? John was widowed after a happy 31-year marriage and has told me he will never marry again.

 No, John! Many people, both men and women, in their 50’s and 60’s, don’t want to marry again. I hear that over and over again. They want a long-term relationship or perhaps living together. Then again, I always laugh when someone who told me a year ago, they are “never” going to marry again, calls and tells me they are engaged. So, never say never!

3. She messages me and we have great chats. Should I ask her out?

Oh my gosh, YES! Time’s a-wasting here. The whole point of online dating it to meet in real life—and chatting is getting you nowhere!

4. Why am I getting low quality men online responding to me?

 Ok, I can think of 3-4 good reasons. You are on the wrong dating site/app, your photos are poor quality and boring, you need help with your dating profile as it’s vanilla or your messages (or lack of them) don’t stand out. Hi, how are you? That shows zero effort and is even worse than sending a heart/like/wink.

5. Why have I had no dates online? (a common question)

See my answer to #4 as that sums it up. Or maybe you are negative in your profile---you wouldn’t believe the things I’ve read online as I help clients with online dating. Examples: Making an offensive political statement, talking about a bad marriage, or how bad the dating site is that you are on. Positive people attract……positive people!

6. Laura, 49, had a fantastic first date with John, 51, three weeks ago. Now he is just messaging her and claims to be super busy at work. Her question: How long should I wait for the second date? I really like him!

 Laura you have two options here: Cut bait as actions speak louder than messages. Or, specifically ask him to a concert or an event with a specific date. Example: Hi Mike, I have tickets for the Red Sox Friday against the Yankees. Would you like to be my guest?” You’ll know from his reply (or lack of) if there is any interest on his part in a second date.

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