Should High Income Woman Risk Friendship by Dating the Handyman?

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DEAR MIDLIFE BACHELOR: I am 46, never married, have an advanced professional degree, and make good
money. I’ve dated my share of professional men, and never found anyone who felt “right”. I come from a modest background … smart parents, but no degrees. I have over the past year become really good friends with my handyman who is the same age and divorced twice. We get along incredibly well and I adore him. We do lots of “friend” things together, and he usually includes his son and daughter when he can. His son (21) keeps dropping hints that there is more, but aside from hugs and an occasional neck-nuzzle … nothing. I make about 3 – 4 times what he does, and am financially stable. He has nothing courtesy of his last divorce (about 4 years ago — she dumped him). We are both ok-looking and I wouldn’t say that he’s out of my league physically and he’s definitely not a player. Any advice or can you help me diagnose the case? I don’t want to miss out on something good or ruin something because I haven’t figured out that he’s just not that in to me. Angie

 Hi Angie – thanks for writing in. One motto of is ALWAYS GO FOR IT … so that is my core advice for you. Since your friendship with this man is obviously important to you, then you probably want to tread carefully just in case he is not into you. Depending on your own personality, I suggest that you drop a hint or two, and then see how he responds.

The “drop a hint” approach might mean that you say something to him like, “I wonder what would happen if you and I ever hooked up?” … or maybe you’d give him an unexpected compliment like “You know – you are looking pretty hot today” … or basically say something that fits the situation, yet steps up the heat.  An alternative to saying something is physically doing something that steps it up – like giving him a peck right on the lips (assuming you don’t usually do that).

Once you’ve dropped the verbal or physical hint – pay very close attention to how he responds. If he says anything that in any way changes the subject or shuts the discussion down, then you’ll know he only wants to be friends … and you should definitely be prepared for that. Recognize, however, that he also could respond with something unexpected and nice. You mentioned that you make 3X to 4X what this man makes – and frankly that makes some men uncomfortable … so also consider that if he rejects you, it might not have anything to do with physical or mental attraction, it could also be that he is intimidated by you financially. The converse of that is – your money might make him want to be your houseboy. ha ha

All joking aside – what I’m really suggesting is that you take whatever steps you are comfortable with to GO FOR IT … and be prepared for whatever the reaction brings. Don’t overbear – else you might lose the friendship. Good luck – let me know what happens!

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About the Author

Midlife Bachelor chronicles lifestyle, dating, and relationship experiences and advice to avoid a midlife crisis. Readers like you are often beyond young adulthood in their 30’s, 40’s, and 50’s that want to understand how dating, sex, relationships, and love fit in with our lifestyles.