A
male
age
36-40,
anonymous
writes:I’ve got myself into a sticky situation and I don’t know what to do - please help!I have this female friend I have known since we were kids. I’ve always had a slight thing for her. She’s stunning, a genuinely nice person and an all around good girl. I know she has had a thing for me in the past too. However nothing has ever materialised between us as I think we both didn’t want to loose the friendship. A part of me always thought she is marriage material and I guess I just wasn’t ready to take that path. I moved away for a year for work and have recently come back. Since then my feelings for her did grow again. I did hint that I liked her but I assumed she wasn’t interested. I then accepted it and started getting over my feelings.Because of this I started dating another woman. We have only been on a couple of dates, but she is lovely. I do like her and decided I want to keep trying with her. However the other night i went out with some friends including the above female friend. We both got very drunk and ended up at her place. Towards the end of the night everyone left and it was just me and her left. I ended up kissing her. I felt like I couldn’t help myself at the time. We ended up in her bed. We didn’t have sex but did everything but. It was incredible. Since then I can’t stop thinking about it and thinking about her. She wanted to have sex but I said no. It’s not because I didn’t want to. But I felt bad for the other girl. My friend also told me before we went to bed that she doesn’t do casual sex and it’s against her morals. I wanted to respect her and realised she was drunk and it was probably not a good idea. So when she asked I said no. I care about her and wouldn’t take advantage of her like that. But I was also really drunk. Problem is I don’t know what the other night meant to her. If anything. I think she likes me but is waiting for me to make the first move. However, I’m terrified. I worry about loosing our friendship. I don’t want to hurt anyone. I don’t know wether to keep seeing the new girl and see how that goes. Or let my friend know my feelings and see what happens there. None of them know about each other. I feel like a scum bag who is dating two women at once and being all secretive about it. Me and my friend are spending a lot of time with each other lately, but I feel like I have to hide the fact that I’m dating someone else from her. Even though me and my friend aren’t officially dating.The woman I’m dating is a lovely woman. But she is 6 years younger than me. I’m at a time in my life where I am ready to settle down and marry and have kids. I worry she isn’t in the same place as me. Whereas my friend is the same age as me. My feelings just seem all over the place the last couple of days. I can’t keep seeing both of them as it makes me feel like crap. But I don’t know who to choose. I see pros and cons in both of them and feel very conflicted. Should I act on my feelings for my friend or continue dating the new girl and see what happens?
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female
reader, Alwin  +, writes (29 June 2021):
 you already know what you should do, stop seeing the new girl, shes young not ready to settle down and you are. As to the old friend, you like each other and seem to have chemistry. Go for it. The whole " i dont want to lose our friendship" is a risk, but theres risk in every relationship, some exes become good friends, others I never want to see again, just dont be a dick in the relationship and even if it doesnt work out you can still be friends.
A
reader, anonymous, writes (23 June 2021): This topic is one of the most common among topics here at DC. There are a few things you must consider when you transition from a platonic-friendship into a romance. I know there is no one-size fits all answer to this dilemma; but there are some general rules we should always consider.
Male-female friendships that have a flirting element often leads to sexual-tension. Even in gay same-sex friendships; that can develop into something that challenges the steadfastness of the platonic boundaries you've set.
Sometimes it's more or less a building curiosity, mixed with fantasy..."I wonder what it would be like if we...!" You push two single heterosexual-people together, approximately the same age, and of the opposite-sex; and you will likely get some sexual-tension. It's often dependent on the timing and circumstance. I am not making the argument that people of the opposite-sex can't be just friends. Save that for another discussion.
What makes it a "friendship" is respecting certain boundaries. Lines you never cross. What often happens when certain boundaries are crossed is that it doesn't necessarily become a true-romance; but ventures into the territory of "friends with benefits." This is having the cake and eating it too. You can have one foot in each camp...platonic-friends vs being a dating-couple. Throw in the availability of sex for good-measure. There is a certain opportunism that infects such a set-up. It usually taints the friendship, and it can often lead to unnecessary drama. One decides they one to go-back to where things were, but one has now become romantically-attached, or infatuated. Now we have a mess on our hands.
The usual outcome is, one will pretend to revert back to where things were; all the while pining and craving for more than being "just-friends!" They'll probably end-up here at DC, lamenting their story of an unfulfilled infatuation towards a friend; with whom they unwisely crossed a line. Now the other party wants to step-back to the way things were. You'll feel betrayed, and extremely jealous; when your best-friend/object-of-infatuation is dating and boinking somebody else! It's heartbreaking! Even infuriating! Then you'll become a wedge and protagonist. Competing for their attention, and testing their loyalties. That's so pathetic!
Now comes that element that causes drama. You're sending-out some pretty strong signals to both women. You're using one as the backup-plan; and the other, you're still somewhat holding her on the hook. Always dancing close to the edge; but not quite crossing the line. Going to bed, while drunk, is opportunistic. Using alcohol as an excuse; and for the sake of liquid-courage. Wrong on all counts! As a man, you shouldn't take advantage of an intoxicated-female; because her faculties are impaired, and the confirmation of consent becomes blurred. She may not be sure; or can change her mind. Guilt and remorse has a way of sneaking-up on you. I commend you for your self-control, and decision to use restraint under those circumstances.
Poop or get off the pot, my friend!!! If you want to take things to another level; be honest, and get it out in the open. Having sex before there is an honest discussion and a complete understanding between hearts; that is just seeking sexual-pleasure, and/or simply satisfying a mere curiosity. If there are deeper feelings, they should be discussed and exposed. Weigh the pros and cons of whether the relationship is better remaining as it is; thereby, keeping sex out of the equation.
Do not string the other woman along; while your heart and mind is focused on somebody else. She's not some consolation prize or second-choice you can selfishly/conveniently place on a backburner; while you wait and see if another person of interest might want to explore being more than friends. Waiting to make sure it's a sure-thing to protect your ego and pride, while avoiding flat-out rejection. As if it's just a matter of you either working-up the nerve to speak up; or pending some drunken-night you'll finally wind-up in bed together, and having sex with your friend.
You're toying-around with someone else's affections and feelings; while you sit on the fence. You have no right to do that to her...to either of them. In fact, it's a bit conceited to think you're the one with all the choices to make.
Kindly let the other woman go, you have no established-feelings for her. Don't allow too much time where she becomes emotionally-attached; and has to undergo heartbreak to let-go. Meanwhile, get the matter between you and your friend under discussion and consideration; before you start seriously dating other women, just to dump them the minute you think you have your lady-friend where you want her.
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A
female
reader, Honeypie + ♥, writes (23 June 2021):
 I think you need to end it with the new girl and give the "old" girl a shot.
You should NOT start a relationship (with the new girl) if you SO early on are willing to cheat. Doesn't matter if you didn't have "full-on sex" you did things that aren't appropriate when dating (unless it's with your partner).
If I were the "new" girl and I found out you cheated I'd dump like a rock. Most sensible women would.
You were WILLING to gamble a potential relationship and future for the opportunity to mess around with the "old" girl, which means you aren't THAT invest in the new girl.
Don't be a dick.
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A
male
reader, kenny  + ♥, writes (23 June 2021):
 I think in your heart of hearts you know what the correct thing to do would be.
I think you should finish things with the woman that is 6 years younger than you. Your feelings for your friend supersede the feelings you have for her, and the longer you leave it the more upset and hurt she will be when she finds out your seeing a lot of your friend.
By your own admission you say that you are at a time in your life where your ready to settle down and have kids, and she isen't. That says it all really, so do the right thing and cut her loose to avoid unnecessary complications further down the line, where potentially you could risk losing both of them.
I think you should act on the feelings with your friend and see what transpires. Just take things nice and slow and just see where the path takes you.
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