Monthly Archives: September 2015

“Jaw With John” – Don’t Overthink After-Work Drinks

I recently ran into an old friend (and former colleague), and we set up a date to have after-work drinks in a few weeks to catch up.

Three years ago I asked her out on a date, but she declined because she was in a relationship.

Last year we were scheduled to do drinks (as friends) and her boyfriend vetoed it at the last minute, saying he felt uncomfortable.

I had forgotten that. How should I ask if he’s now comfortable with it, if he’s even still in the picture? — Ethically Conflicted

Dear Conflicted:

You’re an adult. She’s an adult. You don’t need to ask if she is still with that boyfriend. She is capable of making her own decisions and that should tell you that it’s OK for the two of you to meet up.

The purpose of said after-work drinks is to find out what each of you has been up to since you last saw each other. Don’t overthink it. Said boyfriend might be out of the picture. You won’t know until you see and talk to her. And if he isn’t, then this rendezvous might be canceled again.

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“Jaw With John” – Wedding Gift Dilemma

A friend of my daughter’s (and not a particularly close friend) is getting married in a month.

I have been invited to the wedding.

It is more than a three-hour drive, so I’ve already made up my mind not to attend.

I have only met this young lady one time.

What is my socially correct obligation? Is it necessary for me to buy her a gift? I am not a stingy person, but the going rate for cash gifts is around $150 in our area. Your thoughts are appreciated. — Wedding Vexed

Dear Vexed:

You don’t have to attend if you don’t want to. Politely decline and be on your way. Furthermore, since you are not attending it is not necessary for you to buy a gift, let alone $150.

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“Jaw With John” – Block That Bitch

I have been in contact with an old high school friend for nine years. I do not wish to be in contact with her and I told her that via email.

She ignored my request and emailed me back against my wishes. She called me at 5:30 a.m., knowing I did not like her calling at that hour.

This person is unreliable. She does not do what she says she is going to do. She is irresponsible and, frankly, gets on my nerves.

I have done everything to end my contact with her and she ignores my requests to leave me alone.

What do I do? I never answer the phone when she calls. — Frustrated

Dear Frustrated:

1) File her email as SPAM.
B) Block her phone number.

Done.

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“Jaw With John” – Engaged Friends Are Eager To Get You Married

My boyfriend and I have been together for three years. I am 24 and he is 27. We have enjoyable, well-paying careers, own our home and are busy redecorating. We have had a number of friends get engaged within the last year and are planning weddings.

Almost all of these couples feel that because they are engaged, we should be engaged too. Every time I am with any of them, they ask when we are getting married, when he is buying me a ring, etc. Even my single friends and his family have started asking.

Neither of us is in a rush to be married. Our lifestyle is very different than that of our engaged friends. We are not as eager to be married as they are. We can still do all the things we want to do without signing a marriage certificate. What do I say to these people to get them to stop asking? I’ve already tried “We aren’t in a rush,” and it doesn’t work. I don’t feel I owe them a huge explanation. I just want something that may stop the repetition. — Wondering

Dear Wondering:

Tell them, “we will get engaged when we are ready to get engaged.” Then stare blankly at them for five full seconds to physically indicate how done you are with this line of questioning.

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“Jaw With John” – Older Man Runs Into Age Difference

*Author’s Note: I really found the header image too funny not to use.*

I’m a 61-year-old guy. I’m not married and I have no children. I regularly run into this cute girl (who is about 25) at a park where we both work out. We make passing comments to each other. Most of the time she is friendly toward me. I would like to ask her out. Do you think our age difference is too great or would it be OK to ask her out? I am in good shape because I work out most days, so I look about 10 years younger than I am. — Older but Young in Charlotte

Dear Older:

Here’s the thing: you need to build up a rapport with her before you ask her out. Don’t be that creepy old guy who hits on younger women randomly. Talk to her first. Maybe run with her and then you can casually see if she’s interested in you/available/wants to go out with a much much much much older man.

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