The Unintentional Tease

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DEAR MIDLIFE BACHELOR: I am a 45 year old man, never been married. I haven’t been in a relationship for six years, not even dated. I have a lot of female friends that I am very fond of but I just seem to have lost the ability to “woo” them. I suffered a serious bout of depression after my last relationship and that doesn’t help.I have recently moved from my town, 100 miles away. One of my female friends, who I am attracted to and always felt


would be a great match, seems to be one who likes to set the agenda. I didn’t see her that often, but when I would, she would seem very affectionate but I was too timid to really push the envelope to a physical overture. She is very affectionate with all the men in her life it seems. I assumed that was just her way. As I was moving, I decided not to pursue it.

Well, I was coming into town for a party and she invited me to stay with her. She had been drinking at the party and when we got to her house, she seemed more physically affectionate than before. She showed me the bed (in another part of the house from hers) where I was to sleep and she had me get on the bed. She started cuddling with me and then would get distracted by a cat or something else. As I reciprocated with kisses on the neck and some tenderness, she would not back off but just get distracted. She then said she was leaving to her room to take her contacts out and for me to get under the covers. I did. She came back in her pj’s and got in with me. She then started cuddling and she climbed over me with her clothes on. Then she said she was going to bed, just like that. I asked her to stay in this room, but she left. I wasn’t sure whether to go to her room or what. She didn’t invite me. I just stayed in my bed and left first thing in the morning. She didn’t allude to anything happening.

I just don’t have the mental or physical stamina to play “games” in these situations. Did I drop the ball somehow? Should I have been forceful? She has a strong personality and is very independent so I figured she would appreciate a slow approach. It came across as some sort of “test” or “tease”. Ideas? She is in her late thirties by the way and never been married that I know.

MLB ANSWER: There are a couple of points-of-view here that I’ll go over – but really what I gravitate toward in cases like this is FATE. In other words, the situation developed … things did not happen … therefore that is the way it is supposed to be. FATE – plain and simple. This is my opinion at age 44.

Now if you instead asked me the same question when I was in my early 30s or younger – I would have told you that no woman could have possibly escaped what you described without either getting laid, or slapping my face. I would have simply said something like, “You’re not going anywhere until I say you’re finished.” Of course, this assumes she won’t press charges. ha ha

I personally think that she was interested in focking you … but just didn’t want to put pressure on you … hence the “distraction” sequence you described. I don’t think any woman would get into her PJs, and then cuddle up with you if she wasn’t even remotely interested.

You said that she has a strong personality, and is very independent. You also said that she is very affectionate with all the men in her life. My point is that she could very well be an UNINTENTIONAL TEASE … which means that she was just behaving in her way without any underlying intentions whatsoever. Does that make her a bad person? No – it makes her an unintentional tease. [Intentional teases are bad, by the way.] Just recognize her behavior in the future, and know that it means nothing.

Okay – so I offered up a number of competing points-of-view here. My best answer was my first – FATE. It did not happen with her – and so that is FATE. Don’t over-think it, just move forward. Besides – if you had sex with her, it may very well have negatively-impacted your friendship with her. I guess at age 44 I’m getting to the point where I value really good friendships above everything else.

Now let’s address your very first paragraph where you mentioned that you have gone through depression, not dated for six years, and feel like you have lost your ability to woo women. If you feel like you are ready to get back into the game, then recognizing there is a problem is 50 percent of the solution. The other 50 percent of the solution is taking proactive action to get yourself back on track – and that is exactly what the Dating Advice section of is all about. I highly recommend that you check out these sections of this site:

1) Midlife Bachelor Personal Makeover will help you fine tune your appearance and your attitude – both of which are necessary to date successfully today.

2) Develop a Strategy for Midlife Bachelor Success will help you think through the various steps necessary to meet the right woman. There is a fair amount of trial-and-error here – and it is fine to make mistakes, as long as you recognize the mistakes and take the appropriate corrective action. It is all about fine tuning the machine – and YOU are the machine.

The section on Fundamental Truths about Women and Midlife Dating Today would also be good for you – just as a reminder of what is out there.

Remember – with respect to individual relationships and women, FATE is exactly that. Don’t be offended by fate … use it as part of your individual learning experience. Simply take it all as a data point, and move forward with your life. Let me know how it goes.

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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.