“Should I Go Out With My Dead Friend’s Brother?”
Just before we all turned 18, John was killed in a car accident. Mary was obviously devastated. She withdrew, and we didn’t hang out as much anymore. I think it was too painful for us to hang out together, without John. The grief was unbearable. There were nights that I would wake up to the sound of John tapping on my window (as he did almost daily when he was alive). I soon moved out of state, and Mary and I lost touch.
Fast forward 12 years. I’ve never forgotten John and Mary. Actually, I’ve thought about John at least weekly all these years, and missed my friendship with Mary. Last year I moved back to my home town. I ran into Mary a couple of months ago at the grocery store. She walked right up to me and we hugged and cried. Our friendship has started again, just where it left off before John died. She is even working in the same office building as me now, so we have lunch together most days, and go out together on the weekends.
This last weekend was Mary’s 31st birthday. She invited me to go out to celebrate with her and some of her friends. When she came to pick me up, her little brother, Max, was with her. My heart dropped to the floor when I saw him. Max looks just like John. The resemblance is uncanny, and frankly, it shook me up just a bit. It was like seeing a ghost. Max said he remembered playing video games with me when he was a kid and how much fun I was to be around back then, and he gave me a big hug, and … I felt something.
The attraction was apparently mutual. Sparks were flying all night. On Monday morning, Mary told me that she could tell that Max was diggin me, and asked what I thought of him. I told her the truth – he’s hot, but I didn’t want to cause any problems with our friendship. She said she would not have any problems with us going out. So she gave Max my phone number. He just texted me asking if I want to get together for a drink this weekend. Should I go out with Max? Or is this the whole age difference / resemblance to his brother whom I once loved very much thing just too complicated? Please help. — Too Old to be Crushing Like This
Maybe the age difference between you and Max is too great to overcome — there are differences between a 25-year-old guy and a 31-year-old woman — and maybe Max’s resemblance to his dead brother whom you loved very much will be too freaky for you to get past. But! Maybe neither of these things will be any big deal. Maybe Max is mature for his age; maybe losing his brother when he was 13-ish shifted things for him in a way that matured him faster than other boys his age. And maybe knowing Max as an adult will give you an appreciation for him that is different than your memory of his brother whom you last saw when you were 17.
You won’t — and can’t — know what your feelings will be toward Max unless you spend some more time with him. All you know now is that you are attracted to him, feel chemistry with him, share some personal history, and are forever connected to him by simple virtue of having grieved the loss of his brother whom you once loved. Instead of being weird, maybe all of that is a foundation for what could be a great relationship. Maybe it’s not. Maybe you’ll find you’re better as friends. But you won’t know unless you go out with him and see.
What’s the harm in having a date with Max? As long as Mary has given her blessing and assured you it won’t negatively impact your rekindled friendship, how does going out on a date with Max carry more risk than going on a date with anyone else you might have a mild crush on? It’s not as if you were married to his brother or that you even dated seriously. It’s not like his brother just died last month and you’re disrespecting his memory by moving on too quickly or trying to hold on to what you recently lost by dating his brother. You have processed John’s death. You aren’t under any illusions, I don’t think, that Max is John. So I say go out with him, see where things go, and don’t put too much pressure on yourself to figure it all out on the first date. You’ll know in your gut after a few dates whether there’s something worth exploring with Max or if this isn’t any more than a friendly, mutual attraction.
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If you have a relationship/dating question I can help answer, you can send me your letters at [email protected].


I have a sister that I resemble quite a lot. I personally have a policy that I don’t date anyone she has dated no matter how it ended because I feel that our physical similarities are too great for people to realize our personality differences and fully appreciated them. I worry you might be doing that in this case. You didn’t mention ANYTHING you liked about Max except that he looked like John. I agree that you can’t know without getting to know him better, but I really caution you to get to know the real him. You’ve had this idea in your head for over a decade of what John would have been like, now there is someone that looks just like him. Don’t try to force Max into the idea of John that you have in your head. Get to know him for him
WWS! Sure, there’s a lot more going on that a “typical” first date, but life and love are messy, complicated things. It’s great that you’ve reconnected with your old friend as well.
Are you just wanting to date Max because he reminds you of John?
Much in the way you don’t want things to be awkward between you and Mary if you start dating Max, you don’t want them to be awkward if you start dating, maybe even get serious, and then stop. Also, if you go on a few dates and realize he’s not all that great for you, be prepared for that awkward conversation with Mary on why her brother is not date-worthy (since I’m sure she’ll ask how the dates go). If you think that your friendship with Mary will stay strong thru all the different scenarios that come with dating her brother, and you’d be cool still seeing quite a bit of Max by virtue of being Mary’s brother, go for it. But if you think it may rock the friendship down the line, particularly if you and Max should get serious and then break up, you may want to play this one safe and pass.
I don’t like this one bit. Mary may be okay with it but I’m not. Are there no other available men in your town? You have to choose your dead boyfriend’s younger brother? You mentioned nothing about him other than he reminded you of John. Sparks mean nothing, use your head, not your gonads. It’s creepy.
Eh. My friend’s boyfriend died tragically and accidentally, and a year later she started dating his best friend, they’ve been married for almost a decade and just had their first child. These things do not happen often, but they do happen.
I don’t see the harm in going out with him. Just make sure that deep down you’re not expecting him to be like his brother. I know a lot of time has gone by, but young love has a way of sticking with you, and it wouldn’t be fair to him if you were secretly hoping he was someone else.
I know this is different, but Wendy’s response really made me think. Do you guys think dating a younger man in your 20s is really a problem? I recently started seeing someone 4 years younger and everything seems ok (by ok I mean its fantastic), but sometimes it makes me really nervous that he is so much younger.
I’m dating someone younger, too. I think if you are on the same page timeline-wise, and he is an emotionally mature person, then you can easily make it work. The guy I’m dating is considerably more mature than some other dudes I’ve dated who are older than he is.
I don’t really have a timeline. I’ve only been out of school for a year, and was really enjoying being as non-tied down as possible until I started seeing this guy. That said, I may feel different in a couple years when I am pushing up closer to 30. Its just really hard for me to tell how important a timeline kind of thing may become to me and its especially hard to talk about it because I don’t know what one would be if I had one.
No, I don’t. I think once you’re into your twenties and up, age really doesn’t matter among consenting adults. 6 years is nothing, and 4 years is even less of nothing. Peoples’ maturity levels are an individual thing unrelated to your physical age. It’s much more important to find someone you compatible with in maturity than someone who is physically similar in age.
I don’t think so. You just have to make sure that you’re at the same emotional life stage. Some people are an old 24- they’re done with the party scene and are a little more settled- other 24 year olds are out at the bar till 2am every night of the week (there are also people who fall somewhere in the middle). As long as you know which of those you are, and which he is and are ok with those, then you should be good.
I don’t think the age difference is a big deal at all. I dated a guy who was 10 years younger than me (26/36) and although I had some reservations at the beginning, it turned out to be a non issue. It just depends on the people involved. I have noticed that people tend to think its a big deal when the woman is older, no one has a word to say about a woman in her mid twenties dating a guy in his early thirties.
I dated a guy 10 years younger when we were lab partners in grad school. Then we got married. It’s been 27 years since our first hang out 22 years of marriage and we have 4 kids
And are very happy. Highly recommend treating people as they are not a their ages.
I met a guy when I was 28 and we really hit it off. After a few dates I found out he was 24 and that gave me pause. But! We got married about 6 months later and just had our 44th anniversary. Maybe you’ll be lucky, too.
I would also just make damn sure this resemblance of the dead brother isn’t driving your thought process here… I think it may be playing more of a role than you realize.
Haven’t read the letter, but it’s a no.
One of my mathy friends recommends not dating when the age delta is greater than the number of years the younger is older than 18.
I say go and be honest with him. You’re not sure what you want from this but you would like to get to know him better. And like others have said make sure you’re not making Max a replacement for his brother, he’s his own person and you need to make sure you’re attracted to him as Max and not as some guy who looks like someone you used to be attracted to. However, you won’t know that until you actually hang out with him more.
When I read the headline, my first thought was “No! What? Are you serious?” but after reading the letter I agree with Wendy. Siblings tend to share some personality characteristics, and that is probably as attractive to you as his similar looks. Is Max similar to John in other ways besides looks? I mean like a similar sense of humor, work ethic, similar values, etc. If so, obviously that’s the kind of guy you are most compatible with and gravitate to. Why not give it a shot? Maybe it was meant to be.
If you are asking about it being complicated – sure it is – but that is just how life goes. If the age difference becomes a problem really depends on the couple – will you find shared interests? have a shared sense of humour? accept each other and enjoy each other’s company? You’ll know these answers after you date him.
As for the looking like his deceased brother complication – the real complication in that story was Mary – and Mary is totally fine with it. You aren’t the teenager you used to be when John was alive – and Max certainly isn’t the little brother playing video games anymore. Get to know Max for who he is today and if you like Max and Max likes you – then congratulations. I think it could be lovely for you.
I think you should go for it. It seems like enough time has passed that you have grieved for John and have moved on. Like everyone else has said, you just have to be sure you want to know Max on his own terms (and not as a replica of John).
The age difference issue is bewildering to me. In our society it’s discriminatory, older guy-younger woman is acceptable but the reverse raises eyebrows. When I was in my 30s I dated some women that were in their 50s. They were more settled into a life style that suited them and fantastic in bed. In the case of the LW the difference is small and if the relationship (to be) lasts it will only be a problem to some snoots outside.
One couple that we’re very close to are 10 years apart. He’s the younger one and took on her 2 kids when they were little and was and is a great parent. They’ve been together for over 20 years and now look forward to being grandparents.
Bottom line is: Don’t allow the small age difference limit the potential for happiness. When your drawing social security benefits it won’t mean diddly.
The only reason NOT to go out with the man in question here that I would have thought was totally legit would be if Mary was totally opposed to this — and you wanted to maintain your renewed friendship. But she seems to be all for it. Enter it casually and see where it goes.
I, too, have a dead lover from my past… (Killed by a drunk driver — he wasn’t even in a car, but was a pedestrian…) And if he had a kid brother who looked just like him and was totally into me… I’d totally have to see where it goes, too. Sorry about your loss. I never really got over Kurt’s death either. Even though we’d been broken up for years due to logistics — he was older by four years and graduated college when I was but a freshmen — we had only recently reconnected (epic phone calls…) and so I now often play the cruelest game of “what if..?” Yeah, I was so into Kurt. And the cherry on top was that he was so successful, came from money, amazing job… Who knows how much better my life would be had some fucked-up cunt simply NOT driven home that night.
So, yeah. I say go for it.
In ancient Jewish law, if a woman was widowed, she was required to marry her husband’s brother (unless he rejected her).It was to carry on the brother’s name through the children. Of course you weren’t married and you may not be Jewish but for some reason, I just thought it might be interesting to know that it was seen as the ethical thing to do.
I thought the OP was a guy, but either way, I see the familial issue more of a problem than the age gap. If it ends up being just a bit of fun, it could still irreparably damage the friendship with the sister
Nobody else suspect this story is fishy?