The “Friends with Benefits” Landmine

People write in to ASK MIDLIFE BACHELOR with questions.  An index of all Q&As is located on the ASK MIDLIFE BACHELOR INDEX page. Email your question in complete confidence to [email protected].

DEAR MIDLIFE BACHELOR:  I had an absolutely wonderful first date Saturday night with a gal I met online. She seemed to be just as impressed as I was. She even said I was “cute.” She and I both agreed it was an excellent date. I was completely impressed. However, now she says I need time to “heal” from my recent divorce. I don’t want to “heal” I want to bounce back, and get back up on the horse. She is not my first date since the divorce. However, I am still having court issues with my cheating ex spouse. On a side note, we talked many hours, almost everyday before our date. And we talked a little bit over the phone, while I was on the lake bass fishing. It seems like we really, slowed down after the initial first couple of days after that great date. How do I salvage this relationship? JP

MLB ANSWER:  Let’s look at the facts first. Your date told you that you need to heal from your divorce. This is a clear sign that you are discussing your ex-wife or your divorce too much during the date – otherwise she would never have said that nor gotten that impression, right? The other thing I notice is that you might be uncomfortable with the whole mechanical aspect of dating – I say that because you said that you and your date “agreed it was an excellent date”. What I mean here is – I don’t think it is typical to survey your date at the end of the date … “how did I do?” … “was this a good date?” … “do you agree this was an excellent date?” I’m joking here a little but my point is that it seems like you need to focus on putting your past behind you, and just relaxing when you go out on a date. Don’t over-plan the date … don’t create a long-term agenda for someone you will go out with for the first time. You have to recognize that in the single’s world, many times we don’t get a second date … and the reason for that may or may not have anything to do with you. You just learn to take things less personally after a while.

Since this is not the first time you have written in (see BREAK OUT OF THE “JUST FRIENDS” RUT), I’m beginning to get a good overall picture of where you are at in the MIDLIFE BACHELOR OBJECTIVE ROADMAP: I see you in between the 6 to 12 month arrow and the 12 to 24 month arrow. It sounds like you’ve got your personal appearance working for you … but it appears that you still need to learn to put your past behind you. You clearly already have the ability to go and get yourself a date … but having real fun (versus forcing yourself to have fun) on a date might be a challenge.

Everything I said the last time you wrote in still applies. The Midlife Dating Advice section of this site is absolutely meant for you. I’d recommend you read the Attitude Adjustment/Mental Makeover 2.0 section of the Midlife Bachelor Personal Makeover. And then I’d suggest giving the Develop a Strategy for Midlife Bachelor Success section a look. You are actually doing great in terms of making overall progress – there is nothing to fear, only good times coming which you can celebrate. Frankly I foresee a new, fresh pair of women’s panties coming down, down, down to the ground in your future within a few months. You must live for that precious moment, John ;o)

DEAR MIDLIFE BACHELOR: I would love to be in a relationship.  But since I am not at the moment, I have been toying with the idea of having a “friends with benefits” relationship with my neighbor.  We get along great, are both single and the same age, and are both attractive but could stand to lose a few pounds.  The problem:  He is not interested because he thinks it would be more trouble that it’s worth.  He hasn’t had sex in YEARS and said he’s used to it now and therefore doesn’t want to get back in the “habit”.  Plus he thinks there needs to be more than just a physical relationship, that he can’t have sex for the sake of having sex.  So I feel stupid for even bringing it up with him.  Either he’s lying because he doesn’t find me attractive (I don’t think that’s the case) OR he’s just not into sex as much as me OR ???? I don’t know.

He’s been avoiding me every since I brought it up so I feel like I may have lost one of the only friends I have.  I am really embarrassed that I even approached him, and wish I would have kept my mouth shut.  I thought he’d be thrilled that some woman wanted to give him oral sex whenever he was in the mood and do whatever else he wanted.  What the hell is wrong with me?  I have never been turned down like this before.  It’s really a blow to my ego and hurt my feelings. Anonymous

MLB ANSWER:  Personally, I think your neighbor is nuts.  Or he may have some type of medical problem that prevents him from having sex.  Could be either one – either could cause the behavior that you are seeing.  I suppose it could be that he doesn’t find you attractive, but I doubt that – because you are pretty cute [Midlifebachelor knows this person].  Or at least I think so anyway.  Maybe he has a weird fetish … maybe he only likes short women with an overbite, or something similarly strange?  Could be that as well.  To try to preserve the friendship (which is obviously important to you) I’d say just give the guy some space, and he will probably eventually come around to being your friend again.  If not – then I wouldn’t push it.  But if you put pressure on him to be your friend right now, he might think you are hitting on him … so that is why I say it is best to give him some space for a while.

Don’t let getting turned down damage your ego too much.  Remember – in the single’s world, this happens all the time, and it is no one’s fault … it is just chemistry.  There is nothing to feel bad about.

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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.