Old friends with potential benefits

Miscellaneous and Personal Stuff I Must Share
1

I know this has been done before but this comes with a twist. We met when we were 17 at work. We are now 45 and have been pretty close over the years. We briefly dated and had sexual relations when we were 19. We mutually decided to end the relationship when she went to college out of state.

I went into the military but we still would write to each other. When she graduated she married a friend of mine who she met at about the same time she met me at work. When I finished my enlistment I moved back home as well and got married to a friend of hers that I knew in high school.

All four of us were pretty damn tight for about 7 years but I guess family obligations and the grind of life caused us to drift apart. After my divorce we continued to talk on the phone but my friend was getting a little jealous so we decided to cool it even though nothing sexual was going on.

I met wife number two and she turned out to be a controlling bitch from hell and forbid all contact with her. Yeah I know. The marriage lasted 7 years somehow and there was no contact at all.

After the divorce was final I got in contact with another old friend from high school
and asked about her and how she was doing. He said not good, her husband ( my friend) was dying. I chose not to call because I didn’t want to start a potential shit storm.

He died in mid May of this year and I went to the funeral. I wanted to call her since then but out of respect I didn’t.

Four days ago she called me and we talked for about an hour. She mostly sounded like her old self again and she actually laughed at some lame joke I told.

Here comes the hard part. She was throwing in subtle hints about sex, nothing obvious but I have known her for 28 years and I know the signs.

Questions:

Is it too early to pursue any sexual relationship with her? I already intend on resuming our friendship.

How long should the mourning period last?

I have no idea if she just wants a friend, a friend with benefits, or something more. After two failed marriages I’m not too excited about the prospect of failed marriage number three.

After re-reading my post, it seems a little disjointed even to me. Sorry.

2

  1. Stick with friendship and see where it goes.

  2. The mourning period should last as long as she wants it to last. Stick with friendship and see where it goes.

3

I wouldn’t rule out sex completely but I’d say you need to spend some time with her first just to get a feel for things.

Just from my armchair psychologist view; I’m guessing she’s not feeling too attractive or wanted right now. And that’s important to lot of women. Obviously, she doesn’t want that kind of attention from a stranger so she turns to someone she trusts.

Of course this is just my armchair theory, I could be way off base.

4

I’d say let her know you’re leery of any big commitment first.

Otherwise, it sounds like high time that the two of you got back together.

5

If she wants sex and you want sex then have sex for heaven’s sake. Don’t start worrying about picking out china patterns.

6

But if you must, Wedgewood is always nice.

7

I’ll just bump this once and then let it drop like a stone. The advice is good and since starting out as friends again is great advice, I’ll let her make any move towards me first. I’m in no hurry.

8

There’s nothing wrong with you approaching her as a friend. You can certainly give her a call and say you enjoyed talking, and that if she wants to get together for a movie or dinner, you’d like that. If she starts hinting at something more, indicate your interest but that you don’t want to rush into things.

9

Rekindle the friendship and let her take the lead for if it goes further.

As to whether enough time has passed, I think six months is good. It may be that she’s also wanting to not be alone for the holidays? Does she have any kids? If so, be careful about attending family holiday functions with her. She may be ready to move on, but the kids may not be ready to see Mom has moved on.

10

I thought about that ** FriarTed **.The timing is a little curious and I can understand it since I tend to get mopey this time of year also. She has two kids 22 and 20 and they know me pretty well but yeah, that could be an issue as well.

I’m just going to go really slow with this and see what happens. I invited her to come over to my house this Saturday, so we will see how it goes.

11

For what it’s worth, when I was 20, me and my older brother and sister were actively trying to get mom to hook up with someone.