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Dating at Midlife/Romance At The Dentist's Office?


I was taken surprise and completely caught off guard a few days ago by my dental hygienist (who I've seen 4 times each year for 2+ years). She's always very chatty and must carry the conversation since her hands and various instruments are in my mouth most of the time. We always talk about concerts we've seen and this time was no exception. I mentioned that I just saw a concert with a "friend". Without a doubt I used the word "friend" and "she" at least twice. Especially when I said that "she" makes fun of my tastes, which lean toward older artists. The remark was relevant since Tiffany expressed a love for older artists also. Here's the first twist: I'm 56, Tiffany is 34. Somewhere around this point in the conversation, I heard: "if you ever want someone to go to a concert with you, I'll go." Aside from the obvious and enormous age difference, Tiffany is absolutely gorgeous. I was stunned and had no response, but our conversation continued at it's usual pleasant, rapid pace. I made my way to the front counter to pay and suddenly she came up behind me and stroked my shoulder (there's never been any previous physical contact not related to my teeth). I spent a couple of minutes joking with the office staff and I could hear Tiffany laughing also. We interacted again about people mistakenly calling us some other name. At this moment I'm now attempting to flirt with her. The banter definitely had a playful tone. I have a variety of thoughts running through my head and I'd like some feedback. 1.Prior to this event, I've never flirted with Tiffany or expressed any desire toward her. 2. Don't people my age sometime use the word "friend" instead of "girlfriend" and shouldn't she know that? 3. Do 34 year old women behave this way when they just want a pal to hang out with or does this sound like something with more potential? 4. Why would a beautiful 34 year old want to be with ANY 56 year old man? In conclusion; the aforementioned friend has always been like a sister and I developed a raging crush on Tiffany within about 15 minutes of meeting her. However; unless she reads minds, I've done everything possible to hide my feelings. I have a return visit to see the dentist Tuesday morning and I'm debating about how or if I should proceed with Tiffany. Thank you!

Hi Jim, Yes people our age absolutely use the word friend which can mean many
different things. I wish I knew what 34 year old's think however I'm not one of them so I really couldn't say. Having a beautiful 34 year old is not as uncommon as you might think. Mature (not older) can be intoxicating for some women. They enjoy the maturity, experience, financial stability and having been around the block sexually. Sometimes when we think we're not giving off "clues" body language, a look, what we say and how we say it can be "tells" I'm a believer in conversation. Adult, honest communication. I would not do the concert thing because it's too impersonal. Once you have an established relationship, by all means go to a concert. So your conversation might look like, Tiffany are you game for a light lunch, coffee, or dinner? Your choice. If she accepts then you will see how the conversation goes.  Listen carefully to what she's saying. Is it flirty, friendly, does she touch you when she talks? If all signs are there than you might tell her how you feel and ask her if she's feeling the same. PLEASE brace yourself in the event that she may not feel the same way. I know rejection is hard but you want a business relationship with her if a personal one doesn't pan out. You might reassure her that you're a grown man and if the feelings are not reciprocal you certainly can understand. Than you can decide if you want to go to a concert with her and you will know where you stand. Best of 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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