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Want to ask my wife's sister out for supper...how do I go about this?

Tagged as: Family<< Previous question   Next question >>
Question - (13 February 2007) 17 Answers - (Newest, 17 March 2008)
A age 41-50, * writes:

Dear Cupid,

My sister in law is currently living with me and my wife, well over 5.5 years. I am 34, the SIL is 45, and the wife is 42.

My sister in law is very sweet.

Soon, my wife is taking a trip to London the last Tuesday of next month, and the SIL is scheduled to follow that following Thursday, and me that Sunday.

Well, I wanted to do something nice with my SIL, like take her out to a cool resturaunt when the wifey leaves, but I don't know how to ask her in the right context of being appropriate?

She's very depressed b/c all her friends are with families, etc., and she's still without a man, no guys ever calling here for her, no dating, etc. Some would assume her to be gay based on these interpretations, but I don't think it's the case at all.

However, I do like the SIL, b/c she reminds me of the physical presentation of how the wife looked when I met her 5.5years ago.

My question is, if I ask her, "lets go out(resturant,etc.) and do something?"....my concern is, how could I ask her out to assure we could get to go out and have a good time out?.....

Thanks.

View related questions: depressed, sister in law

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A male reader, anonymous, writes (17 March 2008):

Many guys are attracted to their wifes sister or friend. Why not just say to them at breakfast "I dreamed about you two last night." When they ask what the dream was about just say "Of - forget I said that -it was just a dream." If they then dismiss the conversation forget about having relations. If they insist on you saying just say "We were all in bed together." See where it goes from there.

It worked for me once.

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A reader, anonymous, writes (15 February 2007):

That you are uncomfortable with an innocent request to hang with the SIL...I have to say your carefully placed words do come across as calculating in that you are certain to avoid responsibility.

So by beating around the bush and trying to fob this off as innocent and just doing the brotherly love thing...and then get us to say GO FOR IT...to later come on here and put the blame on us for having your marriage fail for giving you crappy advice for putting yourself in a situation that would invite disaster; I'm not buying it.

If it is indeed harmless then why not run it by the wifey? It just doesn't jive.

That you carefully placed that the SIL reminds you of how your Wifey used to look which equates physical desire...Suspicious.

It's not that we consider ourselves Saints, we just consider ourselves intelligent and not gullible.

You don't want to feel weird? How did this go from I want my SIL to be happy to about you?

Oh...you want...and not have wife know. Wow...that's not about being serpentine by any means.

Oh there we go...it is in fact about you and your sexual urges and about using the SIL for a moment of happiness. Sexual gratification by preying on SIL is not happiness. It's lust.

I think it's not your responsibility; that your SIL is an adult and it's her own, personal life and she has excluded you from it for her reasons should be respected.

Your assigning unnecessary responsiblity of your SIL personal life and have to say; for less than honorable reasons.

Boot SIL out...if she makes your wife feel insecure. Why all the focus on the SIL when it's the WIFE who NEEDS it most. That's why she is Wife.

I say do set the SIL up with a single, male co-worker or friend. How is that for brotherly love?

Best Wishes.

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A female reader, stina United States +, writes (15 February 2007):

stina agony auntHey again Superfly,

Just had another thought. If you're really concerned that your sil isn't with anyone right now, why don't you or your wife invite one of your single guy friends over for dinner. Then maybe your friend and sister in law could get to know each other and perhaps get together. Instead of trying to go out and possibly have an awkward moment (which would make it *really* awkward to live together afterwards) you could make this into something fun for the all of you. Dinner, drinks, games, friends, maybe a movie...

^_^

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A female reader, stina United States +, writes (15 February 2007):

stina agony auntHello Superfly,

You said, "One of my main concerns to get her out is to kind of question her desires about dating, men, etc., b/c I would like to know why hasn't she, a 45 y/o women hasn't been out on a single date with any guy since she's been living with us, and I would like to know, if she has sexual tensions towards women, etc."

So my question is why do you need to ask her to dinner or to a bar to ask her about her personal business? If she wants to talk about it, then it'd be far easier for her to open up to you - if she wants to - while NOT in a public place, don't you think? I surely wouldn't want to talk out in public - with someone who was even scared to ask me to dinner and doesn't want my sister to know - about:

- why i don't date

- why i can't date

- my taste in men

- if i'm a lesbian

- etc, etc...

BTW - why do you want to know? If you're too scared to ask her out, why are you not scared to ask her something so extremely personal? I don't get it. Sorry.

If worse comes to worse, just say "Hey! Do you want to go out to dinner with me so I can ask you about your personal life/dating life/sexual orientation? Just don't tell my wife/your sister because it'd make me feel disgusted." Or you could just say "Hey - I want to know what's wrong with you and why you can't find a man" and skip the dinner altogether. lol

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A female reader, willywombat United Kingdom +, writes (15 February 2007):

willywombat agony auntI don't think anyone here is making out they are saints, just trying to help you before you find yourself in an inappropriate situation that may mess up your marriage or hurt other people.

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A reader, anonymous, writes (15 February 2007):

This is verified as being by the original poster of the question

.......OMG, everyone here is a freakin saint now?

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A male reader, eddie Canada +, writes (14 February 2007):

eddie agony auntSuperfly, your question is hard to read/understand and it seems like you motives are off the wall. Buy yourself a TV dinner and stay home. What are you trying to accomplish with your sister-in-law? That is the big question. Your replies have been convoluted.

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A male reader, jrwest1973 United States +, writes (14 February 2007):

Mention it in front of your wife before she leaves. That would take all inappropriatness out of it.

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A male reader, Ponungalungb United States +, writes (14 February 2007):

Ponungalungb agony auntI decided I need a little more of this action. LOL.

Your question was:

"My question is, if I ask her, "lets go out(resturant,etc.) and do something?"....my concern is, how could I ask her out to assure we could get to go out and have a good time out?....."

Here's my answer*:

Ask your SIL out to dinner and see what she says.

*Footnote:

There's no guarantee she's going to say yes, and if she says yes, there's no way to guarantee that you are going to have a good time.

I'll go back to what everyone else, including me, has said. If your wife is as concerned about her sister as you seem to be, wouldn't it be obvious to include your wife in the discussion as to what would make her sister happy? Not to include your wife in the discussion makes your efforts at taking out your SIL seem somewhat nefarious.

Now, I'm out of this discussion . . . .

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A female reader, NuttyGooner United Kingdom +, writes (14 February 2007):

NuttyGooner agony auntAs I said - if you actually read my answer - Ask your wife - maybe she wouldn't feel so awkward about being on some kind of covert operation - she'll feel more nervous than ever! I'm now not surprised your wife is extremely insecure!

The SIL's friends have pretty much repeated what I said - perhaps the SIL is sick to the back teeth of being probed about her private life.

You keep twisting everyone else's answers - your question was "if I ask her, "lets go out(resturant,etc.) and do something?"....my concern is, how could I ask her out to assure we could get to go out and have a good time out?..."

I answered it by saying, in a nutshell "ask your wife, so she'll at least have an iota of trust in you - and don't probe into your SIL's private life"

I answered your question - just because it is not the answer you want to hear doesn't make my view any less valid. My mother is EXACTLY like your SIL.

"How would the wife feels if she finds out the husband is asking the SIL out on secret dinners?....~means to me of little regard" - Sums you up to a T!

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A reader, anonymous, writes (14 February 2007):

This is verified as being by the original poster of the question

Why are you trying to evaluate innocent intentions or moral behavior here?....

I am not asking for any,"Could you help me do the most normal thing, from your stand-point?"

I gave you a situation, and you don't have the ability to provide me with direction without evaluating the issue of 'marriage,' 'morality,' 'family,' or 'sisterhood.'

Why she won't open up is not about sufficing someone elses business.....It's curiosisty b/c her loniness could be systemic, psychiatric, traumatic, b/c what all her friends are saying is, 'She should be living on her on, and finding her own life-space.'

How would the wife feels if she finds out the husband is asking the SIL out on secret dinners?....~means to me of little regard. The wife is already insecure of the sister being there and often times the SIL feels unconsciously threaten to remain in her place as she lives with us.

Being without a wife or daily LOVE, doesn't mean the 'World is at it's End.'

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A female reader, NuttyGooner United Kingdom +, writes (14 February 2007):

NuttyGooner agony auntSuperfly54, my mother is 47 and hasn't been out on a date for nearly 24 years!

The reason why she doesn't go out on dates (even though I sometimes plead with her to go out and have some fun) is for one simple reason. She just doesn't want to. She's happy with going to work, seeing her friends, and playing around with the cats, just how things are in her life - she doesn't want the complication of relationships to disrupt the equilibrium.

Maybe your SIL's reasons for being 45 and not dating may simply be her choice and knows full well that she doesn't need a guy in her life to make her happy - and why she won't open up is because it is none of your business.

Ever considered that, or are you of the school that every woman has to have a man - no woman is happy on her own?

If she is having concerns, I think she is more inclined to open up to her own sister rather than her BIL, and feeling weird about taking her out with your wife knowing? I am in agreement with Irish49 - why feel weird about your wife knowing if your intentions are as innocent as you say? - imagine how she would feel if her husband was taking her sister out on secret dinners?

Just ask your wife, she will be monumentally hacked off otherwise and like Portulang said, you'll be without a wife with a SIL to ask out!

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A reader, anonymous, writes (14 February 2007):

This is verified as being by the original poster of the question

I don't give a damn about not using family to understand: intentions of other family members, helping to restore balance and happiness for family members, ! I have a to be curious and it's up to me to, etc.

If I have other plans, one thing for certain, is that if a moment with her makes me happy, I am not going to rule out the opportunity from being happy, regardless how short lived the experience maybe.

She's 45 and she should have more going on instead of going to work on a daily basis to a bagel shop, and coming back home to watch recorded daily soap operas.

If she's gay or not, I would like to offer her some comfort to alleviate any pressures from not stepping out of the closet.

She's 45 and life is short and as age advances, so doesn't physical and somewhat, mental health.

Dating preferences?.....She doesn't have a preference less known an idea of a date.

I am doing her a favor, by asking her out, and if she desires something else, then that's another issue.

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A reader, anonymous, writes (13 February 2007):

Superfly, your SIL's desires and her dating preferences, are quite frankly-none your damned business. You have 'other' plans for this woman, don't you? I strongly suggest, you take the dinner 'date' idea and toss it out the window and stop placating your ego. One doesn't use family members like that. Get a grip!

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A reader, anonymous, writes (13 February 2007):

This is verified as being by the original poster of the question

I feel somewhat disgusted to ask the wifey about me asking the SIL out to a resturant/bar, b/c I don't want to feel weird by knowing the wife knew I took her sister out.

I just want to ask her out without the wife knowing from my part.

One of my main concerns to get her out is to kind of question her desires about dating, men, etc., b/c I would like to know why hasn't she, a 45 y/o women hasn't been out on a single date with any guy since she's been living with us, and I would like to know, if she has sexual tensions towards women, etc.

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A male reader, eddie Canada +, writes (13 February 2007):

eddie agony aunt

If this is your sister in law and you have a normal relationship, then just ask her if she wants to go out. The fact you're concerned about this makes me wonder why. It's not a date. She's family and you're hanging out. If this is not true, then you shouldn't ask her to go anywhere.

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A male reader, Ponungalungb United States +, writes (13 February 2007):

Ponungalungb agony auntSuperfly, I think I'd talk it over with the "wifey" before you ask out the "SIL". If you're just doing it to be a nice BIL, there shouldn't be a problem. If you have other intentions, you best be rethinking those intentions, unless you want to end up without a wifey and a SIL.

Good luck!

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