Shortcuts: “I’m in Love with My Gay Best Friend!”

It’s time again for Shortcuts. For every question, I’ll give my advice in just a few sentences, because sometimes the answer to a person’s question is so obvious and the need to hear it so great, being as clear and frank as possible is simply the best way to go.

I think I am in love with my gay best friend! When we first met, I had a huge crush on him, but I didn’t pursue him because I was dating someone at the time. The longer we knew each other the stronger our friendship became. Soon I learned that my crush was gay. Since I’m now his best friend, I hear all about his relationship and let me say I cannot stand his current boyfriend for many reasons. Recently I had a dream that we kissed and did some other freak McNasty things, which rekindled the crush I had on him when we first met! Now I find myself jealous of his boyfriend (because he doesn’t deserve him). He has everything I desire in a man, but he’s gay. I don’t want to tell him how I feel and potentially ruin our friendship, but I feel like I’m going crazy I want him so bad! He once said after a REALLY bad relationship with a female that he was scared and can’t date women anymore. Please help! — A young Hopeless Romantic

Men don’t “become gay” just because of one bad relationship with a woman. You cannot turn your gay friend straight. He is not interested in you romantically and, the sooner you accept that and turn your attention to men whose sexual orientation is better matched for you, the sooner you will start “going crazy” for entirely different reasons (see below, and also every other column on this site).

My fiancé of two years broke up with me, stating he’s not happy anymore. We have been broken up for about two months, but for the last month he’s been coming around daily — basically after work, he’s here for dinner, spends the night, and then goes to work from here. We have great sex and it’s gotten even better since we broke up. I want my relationship back though. What I don’t understand is, if he didn’t want the relationship, why is he still hanging around me? I’m still the same person. I’m confused but my heart has healed thanks to him being around and not totally saying to hell with me. He really doesn’t know how to express himself or doesn’t want to, and I need answers. — Looking for Answers

He doesn’t want a commitment. He wants his freedom while still getting a free meal, literally, plus apparently awesome sex. Why would he walk away from that if you’re enabling him to have his cake and eat it too? If you’re happy with the situation, enjoy it for what it is, but don’t expect this man to commit to you, be faithful to you, or plan a future with you — not as long as you’re sending the message that he doesn’t have to.

I am 21 and my boyfriend is 28. We have been dating on and off for five years, and we have been living together for three years. Although he has cheated on me in the past, the last two years he has remained faithful. Recently, he has started dropping hints about getting married, and I’m just not sure. I have lost interest in being intimate with him, but I don’t want to leave him as we have so much history together — he helped me through the death of my mother and I helped him through the death of his father, and every time we have separated in the past we have always found a way back to each other. I have suggested just being together, but he wants to get married. How do I get over this hurdle? — No Thanks on Marriage

Having a strong history isn’t enough reason to stay with someone — especially someone you aren’t interested in being intimate with anymore. It’s actually unkind to stay with him if you are no longer in love with him and only stay with him because it’s comfortable and it’s all you know. You’re 21 — it’s time to spread your wings and fly. You can’t do that if you continue staying with someone you feel no passion for.


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  1. So he was a 23-year-old dating a 16-year-old, and now that LW3 is actually growing up they’re not working as well? Really, quite shocking. I don’t mean this as a dig to you, LW3, I just think you’d probably have more interest in dating someone who’s interested in dating a grown-up. Wendy’s 100% right on this one.

    1. starpattern says:

      Exactly what I was thinking on that one!

    2. My thoughts exactly. Plus, how sad that a 21-year old is settling for an old, sexless relationship. You should be at least 40 before you do that. 😉

      1. lets_be_honest says:

        Haha! Nice one.

  2. LW 3 – You were 16 and he was 23 when you started dating. Umm no. Just no.

    1. EricaLnyy says:

      Eh, my parents started dating at 16 and 22. Somehow it seems creepier now than it was in the 80s but it really shouldn’t.
      Just saying that shouldn’t be what everyone focuses on. It doesn’t look like it was the best choice for LW3 but for some people it’s fine. That’s hardly the most important issue in the letter.

      1. lets_be_honest says:

        So, I can’t even come close to agreeing that for some people its fine for a 22 y/o and a 16 y/o to date. I’m kinda shocked that anyone likes this comment.
        But yea, plenty of other issues in that letter too.

      2. EricaLnyy says:

        So you’re saying it’s wrong that my parents dated?

      3. lets_be_honest says:

        I’m saying I don’t think 22 y/os and 16 y/os should date. For one, its illegal. I mean obviously it worked out for your parents, but no, I can’t agree that it is ever ok for an adult to date a minor.

      4. Date? Or have sex?

      5. Avatar photo GatorGirl says:

        Personally, I think either. But I can respect others have different views.

      6. Yeah, I’m just curious about people’s views.

      7. 16 is the age of consent in a number of states.

      8. lets_be_honest says:

        I’m going to bow out of this convo after this comment, because I don’t mean to offend Erica at all, but honestly, I’m pretty shocked that anyone would think its an acceptable thing regardless of the possible minimum age of consent.

      9. I’m not speaking to acceptable or not. You said illegal. I’m addressing that claim because, no, not necessarily. But maybe.

      10. lets_be_honest says:


      11. I think there are plenty of things that work for certain individuals that shouldn’t be recommended on a larger basis. It’s great that it worked for your parents. However, I don’t think most people would recommend that a 16 year old date a 23 year old.

      12. Avatar photo Addie Pray says:


      13. Yeah, I’ve used this analogy before, but just because someone’s life was saved in a car accident because they WEREN’T wearing a seat belt, doesn’t mean that it’s a good idea for people to generally stop wearing them. Or that telling someone to wear a seat belt has to be qualified with the idea that sometimes seat belts aren’t safe. Everyone and their lives are unique, but that doesn’t negate things that are generally true. And one thing that I think can be considered generally true is that when an adult started dating an underage person, it often is not an ideal relationship.

      14. Avatar photo GatorGirl says:

        I don’t think LBH was trying to make it personal about YOUR parents, just saying that she personally disagrees with it. And I did a little googling and state legislature is pretty spilt about the age of consent too, so clearly there are people who fall on both sides.

      15. lets_be_honest says:

        Thanks GG. You’re right, not trying to make it personal at all even though I can understand why it would be taken that way. I obviously don’t know jack about her parents.

      16. Avatar photo GatorGirl says:

        No probs! I personally agree with you, and will probably forbid my hypothetical children from doing such, but it doesn’t mean people who have done it are terrible people.

      17. EricaLnyy says:

        I didn’t think LBH was attacking my parents or anything, just voicing her opinion. I just meant obviously sometimes people date at those ages and clearly things work out. And age of consent laws are tough because maturity is not black and white.

      18. lets_be_honest says:

        Thanks for not being offended! I know how defensive I can get on here when people don’t mean to offend me.

      19. Avatar photo Addie Pray says:

        I’ll say it – I think it’s wrong that your parents dated. Just my opinion. For a whole bunch of reasons that I won’t go into, I wouldn’t want my hypothetical 16 year old child (male or female) dating a 22 year old (male or female). It sounds like it worked out just fine for your parents. But I would have not encouraged that relationship. I mean, it also worked out for Mary Kay Fualaau (nee Letourneau) and her former 12-year old student-now-husband (I think they’re still married, right?) but that doesn’t mean I would have approved of their relationship when it started. Obviously at 16 and 22, your parents’ dating wasn’t quite as inappropriate (or illegal). I just use that as an example of a “just because it worked out doesn’t mean it wasn’t wrong when it started” situation. I’m sure your parents aren’t alone; I bet there are a ton of 16 year old girls who dated guys in their 20s, and who went on to have healthy relationships. It’s just, I dunno, I think …. I think 16 year olds shouldn’t date 22 year olds! That’s sound logic.

      20. He was 22 so your entire premise is flawed…

      21. Avatar photo Addie Pray says:

        Fixed it, so I’m still good! Ha.

      22. My mom dated a couple guys in the 20-23 range when she was 16-18. She had two older brothers, their friends were the guys she knew well and trusted.

      23. I agree that it’s not really what we need to focus on in this letter.

      24. Avatar photo barleystonks says:

        I agree with you about the 80s- my husband (who is admittedly significantly older than me) started dating his ex-wife when he was 21 and she was 16, but again, 80s. I tried to spin this into a “see? Always a younger woman thing. Also- creepier than us because I was at least legal to drink.” but he (and his brothers) just gave me the blankest looks possible. They framed it as no self respecting at-least-16 year old girl in the 80s would EVER date someone still in high school. Other people I’ve talked to of similar age seem to back this up. But yeah, definitely creepier now.

      25. TheOtherOtherMe says:

        As someone who was a teenager in the 80s, I can assure you it was just as questionable then. The 80s is not ancient history. Now the 50s, that was a different era….

      26. haha the 80s is ancient history to some because they weren’t born yet! 😉 if you tell yourself that it makes you feel better i promise.

      27. This reminds me of my grandparents who just celebrated their 72nd (!!) anniversary – they are 90 and 99. My grandma loves to tell a cute story about how when she was 16, my grandfather would come to her high school basketball games to watch and cheer her on. We all thought this was sweet till a few years ago when my sister and i did the math and were like, ‘wait, so when Grandma was 16 and playing basketball, Papa was… ewww! 25!’ And then we like to joke about how skeeved out we’d be if we had a 16 year old daughter with some creepy 25 year old MAN hanging out at her high school.

        Also, Grandma makes it very clear that Papa was definitely not doing anything illegal… he didn’t get any sex till she was 18 and more importantly, married! =)

      28. Avatar photo Addie Pray says:

        haha that’s hilarious!

  3. kerrycontrary says:

    I love how LW3 skimmed over the fact that her boyfriend starting dating her when he was 23 and she was 16.

    1. one time i made out with a 23 year old when i was 17.

      it was a fun summer, haha.

      1. kerrycontrary says:

        17 is closer to 18…I don’t know. I just cannot imagine being 23 and wanting to make out with a 16 year old. 16 year olds look like children to me.

      2. haha, well, i guess to your point, i turned 18 in october, and it was the summer.. so much closer to 18? lol

        i have no idea why he did it either. it was stupid. we even “dated”, very very casually though.

      3. Avatar photo GatorGirl says:

        I don’t think I even knew people who where 23 when I was 16 (or 17). I was a junior in high school and that was literally my bubble.

      4. yea, it was a…. weird summer. i didnt “know” 23 year olds either. weird sequence of events…

        and also it was just that summer. that summer is like, *the summer* my friends and i still talk about. i have a whole scrapbook dedicated to it, and i brought it with me a couple years ago when one of the friends who had moved away came back to visit, and it was awesome. we even took pictures with the scrapbook.

      5. The few 23 year olds I knew at 16 were definitely not dating material. And we all made fun of them for still wanting to hang out with us high schoolers.

        Then, when I was 23, I couldn’t imagine anyone my age dating a 16 year old. Of course, at the time I was working at a treatment center for teenagers, and I was super protective of my girls, and none of my friends would even imagine hanging out with kids that age.

      6. Yeah, I used to hang out with a 21-year-old when I was 16ish, and I’d be thinking, “Loser. Get friends your own age!” I also thought he was ANCIENT. Haha.

      7. kerrycontrary says:

        Yeh…I knew a few people in their 20s when I worked at an amusement park. When I was 17 almost 18 I was probably hooking up with people who were 19-20. But definitely not when I was 15-16. I did have a 19 yr old ask me out when I was 15 or 16, but I couldn’t figure out how to explain that one to my parents (and I couldn’t lie to them at that point), so I just blew him off.

    2. To join the party over here–I hooked up with a 25 year old when I was 17. Then he kept calling me wanting to be sex friends, but I turned him down because my other (also 17 year old) friend had a crush on him (noble of me?? But I’d already hit that, sooo not really logical). I also left my coat & bra there,& was gonna count them both as a loss, but then I missed them too much, so I called the 25 year old like 4 months later to get them back. He clearly thought I’d reconsidered his FWB offer (guess he thought “needing my stuff back” was a ploy?) but I was just like, “thanks for washing these! Bye!”

      The end

      1. I think 17 in some states is ok. Like I’m totally nosy so I looked up your state and technically what he did wasn’t illegal. However, that (whether or not it’s legal) depends on where you live.

      2. Most states are between 16 and 18. In MD it’s 16, but if you’re at least 14, there’s a within 3 years rule (the “if a 15 year old has sex with his 17 year old girlfriend, no one goes to jail provided all parties consented” rule as it were). So 14 and 17, fine. 14 and 18, not fine. 15 and 18, fine. 15 and 19, not fine.

      3. yeah, i didn’t look that far in to it!

      4. I only know MD because I went to school there and the 14 and 18 is illegal thing was beaten into our heads to keep the seniors and the freshmen away from one another.

      5. Yeah we have that in my state. People refer to it as the “Romeo-Juliet law”.

      6. I love your stories!

      7. Avatar photo Addie Pray says:

        I love your stories too. Tell us more. Oh oh I have a game — Fabelle, I’ll throw out some random words and you have to tell us a true sex story from your past that comes to mind based on each word. Got it? Your words are: roller coaster, Taco Bell, fire crackers, and bow tie. Go! We need 4 sex stories, 1 for each word. … Come on, I bet you have like 10 sex stories to share. Share them already! Why are you making me wait, this is torture! Egad.

      8. Avatar photo Addie Pray says:

        I guess i’m sort of expecting Fabelle to say she met a guy at Taco Bell who was wearing a bow tie and they did it on a roller coaster on the 4th of july… i dunno. i guess is should get to work. Fucking work, it’s like always there interfering with my life.

      9. Haha!! Fabelle, if you have a story for each one of these, you are my new hero. 🙂

      10. Hahaha AP, I don’t think I can type out all those stories on my phone 😉 (jk, jk, I can only think of 2 fourth of July stories & one–not a story, but a particular person–who comes to mind with the “Taco Bell” thing. I’ll owe you!!)

      11. Avatar photo Addie Pray says:

        come back here and spill it! i live for fabelle stories.

    3. Avatar photo lemongrass says:

      So when I was 16 I dated a 25 year old. He was a coke dealer. It was classy! I was very naive, and he was a really big loser. It was probably the biggest regret of my life but I’ve moved forward and put it all behind me.

  4. wow, i have the same advice for all the letters today- that never happens!

    you all need to move on and go forward with your lives. staying where you are will stagnate and bore you. these chapters are just *begging* to be closed, and you need to be the one to take some control and close them.

  5. So LW#3 was 16 when they started dating? And he was 23?

    Also WWS for the other 2.

    At least it’s Friday!

  6. Avatar photo GatorGirl says:

    LW3, you’d don’t get over this hurdle, you get out of this relationship. Being “on and off” is basically the biggest indicator, in my opinion of course, that a relationship is not long term (ie marriage) material. It’s great that you where there for each other for such devastating events, but they shouldn’t be a reason to stay together NOW. Move on, and don’t date guys who date 16 year olds (yuck).

  7. Shadowflash says:

    LW1, I think most of us have had a “dammit, why did you have to be gay?!” moment. But it’s just a moment, and you have to move past it. It’s not yours to decide whether he’s attracted to/capable of dating women–that’s his choice, and he’s clearly Not Interested. So back off.

    LW2, wanna take a guess as to why fiance wasn’t happy anymore? That’s right, commitment was looming. Notice how he’s much, much happier having the whole kit and caboodle *without* that nasty marriage business hanging over his head? You want a relationship (I presume that means resuming your engagement/marriage) and he doesn’t. There’s nothing else to say.

    LW3, you ramble on a little abut cheating and living together but never say why you don’t want to get married. Even if it’s just “I don’t want to feel 30 and married when I’m 21 and single”, this isn’t a hurdle you just jump over and carry on. Like with LW2, he wants to get married and you don’t. There isn’t a viable compromise here.

    I’m trying not to judge the whole 16-yr-old dating a 23-yr-old thing, since that isn’t what the letter was about, but my “ick”alarm is seriously going off.

  8. LW 1 reminds me of when I first started dating my first boyfriend (now ex) in college, he had a gay best friend who was pretty much head over heels for my boyfriend. It was kind of ridiculous but at the same time, he never pursued or tried to “turn” him gay because he knew there was no chance in hell. I wish the LW would have similar clarity in this situation…

  9. To be so “in love” with a gay friend to the extent that you have to write an advice columnist for help shows a complete lack of maturity. The undertone of the letter is that the LW wishes he would “turn straight” and date her, which is bordering on insulting and disrespectful. He’s gay. Accept and embrace that.
    It’s okay to be attracted to someone. That’s human nature. But adults know how to control their feelings and put them aside when they realize they are inappropriate.

    1. AliceInDairyland says:

      ON FIRE!!

      …except I need you to ask the LW an insightful, reflective question! 🙂

      1. Haha, I don’t think there’s an insightful, reflective question for this LW. She seems pretty far gone.

      2. AliceInDairyland says:

        Touche. Haha.

      3. Ooo OO, I’ve got one… “LW, do you have a pattern of falling crazy-in-love with unavailable boys? If so, this pattern will likely follow you into adulthood, but if you recognize it now and nip it in the bud, you’re taking a big step in the right direction!”

    1. Avatar photo lemongrass says:

      Yes. It’s the new “sweet, sweet love.”

      1. Avatar photo Addie Pray says:

        i, for one, am long over due for some sweet, sweet freak McNasty love. le sigh.

  10. LW2

    I’m sorry that you’re going through this, you’re trying to hold onto something that’s not there anymore. I was with my ex fiance’ for three years, engaged for one. I bought a wedding dress and that’s when the relationship started to deteriorate. A few months after, when I realized that he was on his way out the door and no matter what I did, I was not getting him back, I was able to stop the dress from being put into production and get my money back.

    His relief was palpable, and he was back into my life. I stopped wearing my ring and calling us engaged, and he was all about being with me. Until the fighting started again and he moved out blah blah.

    He doesn’t want a committment. He wants his freedom, and I don’t think he’s in love anymore 🙁 It’s easier to rip the bandaid off and work through the hurt than hang onto something that’s not true.

  11. LW3: Don’t feel obligated to marry someone just because you’ve been together a long time and he’s been supportive when bad things happened. Being nice to someone when their mother dies is the baseline for human decency, not a favor you need to repay with a lifetime commitment. In fact, it wouldn’t be a favor at all – marrying someone you aren’t in love with is one of the worst things you can do to them. Loyalty is a beautiful thing, but your gut (and heart) is telling you that this isn’t the right person to commit to.
    You’re 21! Go and find someone you’re excited to go home to for the rest of your life. Cut this guy loose to find someone who will be excited to see him. Someday, you’ll both look back and be so glad you found the right partners.

  12. LW3 – I got engaged and married when I was 21. But, I was quite sure about it. We’d been dating for 5 years (continuously, not on-and-off). I’d lived on my own from 17-20, and with him for a year when I was 20ish-21. There was no cheating involved, and we were both confident in our choice to marry. And rather than losing interest in being intimate with him, I wanted to spend more time with him.

    Don’t marry him unless you are sure that you want to. No matter how much he wants to marry you, you need to make sure it is what you truly want. Don’t marry someone just because of a ‘shared history’ or because you’ve been together long enough that it seems to be time. Marry because you honestly want to spend forever with him, and because you want mutual things for the future (i.e. kids in x years, no kids, similar financial goals, etc etc)

  13. Avatar photo Addie Pray says:

    I want to know more about these “freak McNasty things.”

    1. Avatar photo lemongrass says:

      It involves a clown, McChicken sauce, bungee jumping, purple socks and googly eyes.

      1. Avatar photo the_optimist says:

        freak McNasty things sound delicious and dangerous all at the same time. Where do I sign up?

    2. sarolabelle says:

      I want to have freak mcNasty dreams…..

  14. LW1: you’re reading way into the fact that your gay friend dated a woman once. It doesn’t matter. You friend is in a relationship, and gay, and there’s no point in telling him you have a crush on him. I have a friend who gets crushes on her gay friends and I think it’s because she’s too scared to date or like someone that would be interested in her and would rather have a ‘safe’ crush. But don’t waste your time on someone who is not only in a relationship, but not into women in the first place.

    LW2: a lot of relationships end because for whatever reason, one person doesn’t see it as a great fit anymore. They can still like you a lot, think you’re great and everything, but still not want to be with you. It’s not always this big blow up of a breakup. Your ex sounds like he wants to have his cake and eat it too. Maybe he feels bad for breaking up, maybe he just wants sex, maybe he’s not over you. But you two did break up so you have to decide if you’re okay with still seeing him. It’s unlikely you’ll be able to move on when you’re still having sex with him.

    LW3: I dated someone inappropriately older than me when I was 16 and we were so codependent. We were always trying to fix each other and it made it that much harder to leave him. But I’m so much better off now. You also sound like you depend on your boyfriend too much in how much he has helped you. You don’t want to get married yet. Just do yourself a favor and move on. You haven’t really ever had time to be on your own. Even though you feel like there is too much history to leave, there really isn’t. If you leave now, you have plenty of time to move on and have a healthier and more mature relationship (because your 28 year old boyfriend is not that mature if he was interested in a 16 year old). Also, he cheated on you before. You don’t need him, and you’ll be just fine without him.

  15. I just have to say, this: (see below, and also every other column on this site). Made me laugh out loud. Well played Wendy.

  16. LW1: I honestly don’t know the purpose of your letter. You are a woman who likes a gay man. Why would you tell him you’re interested? He’s not going to be into you. The fact that you seem to think he’s too stupid to know the difference between being gay and having had a bad relationship make me question how good of “friends” you actually are. Maybe spend less time thinking about how much want him and actually understand what sexual orientation is.

    LW2: He wants sex without the commitment. Duh.

    LW3: If you don’t want to marry someone, then don’t. And I’d suggest ending things since you two clearly have different plans for the future. Marrying someone because you have history is a bad idea. It’s history — meaning, it’s in the past. It’s OK to have had experiences with someone in your post without having to commit to them for your entire life. That’s why a lot of people date various folks but don’t marry all of them.

  17. So BGM – has a straight woman ever crushed on you, or one of your cohort of gay male friends? If so, how’d that work out?

    1. Avatar photo bittergaymark says:

      Yes. Not well for her I am afraid — as she has dated a vast array of closet cases. Not that I can throw too many stones as I myself have had a vast array of male best friends that I fall in love with — all straight. (Though masters of mixed signals…)

      Addie Pray — you rather recently asked why I was so bitter? Um… Mystery solved.

      1. LW1: A glimpse into your future.

        On a casual note, I sometimes wonder why certain women seem to attract, or be attracted to, closet cases. A former work-friend of mine has a history of dating and even being in LTRs with men who later came out as gay, and also has many platonic gay male friends. Is there a certain personality, or personality trait, that creates “fruit flies” like this? (HER term, not mine!)

      2. Avatar photo bittergaymark says:

        Before fruit flies it was fag hag — so the latter is the mutually agreed upon lesser offensive one.

        What’s NOT to like about gay men? They are sensative. Have great style. Enjoy shopping and LOVE to gossip about unattainable celebrity crushes like the two Brads. (Figure it out.) Plus a surprising number of women just aren’t THAT into sex so…

        I kid, I kid… But there IS a grain of truth in that.

  18. Avatar photo bittergaymark says:

    LW1) Actually, all straight men are just one one bad relationship — or even uber bitchy outburst by their women away from going gay. NEWSFLASH: They can flip like that in an instant. Ladies, you have been warned. Unfortuately, it is a one way switch and once they go gay they are that way forever… If only you’d met him first, LW…

    LW2) Obviously his love for you grows with each meal and fuck. Hang in there — in a decade or so he will finally be ready to give you the committment you simply don’t yet deserve. Wanna speed things along? Simply become a better cook — oh, and better fuck as well.

    LW3) I was all ready to tell you to M.O.A. — but then you mentioned history. Yikes. The big H trumps all. You must now marry this man immediately — thus dooming you both to a miserable and sexless marriage. Such is the price of history. Because of it and it alone there is only one thing for you to do — destroy his life. And yours. Truly, you owe it to both of you now. Also, have kids IMMEDIATELY as that always fixes floundering relationships.

    1. i love BGM going the validinator.

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