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Ask Mom & Spawn: How Do I Ask My “Kinda Already” Boyfriend to Be My Actual Boyfriend?

Toni wrote in because she’s been dating her friend for a year now and they’ve both said I love you … but they aren’t officially boyfriend and girlfriend. She had kinda asked him about it before, but is now worried that he will outright reject her and would rather live with the uncertainty. What do you think?

“Hi guys! I love your posts! This is kind of a long story but I’ll cut it as short as I can. I’m in love with a guy, and he knows this and has said it back too. We were friends for a while a couple years ago and eventually I told him I had feelings for him, and we ended up sleeping together and acting like a couple but without actually confirming whether we are one and haven’t ever since. I asked him if it was just sex for him or if there were feelings involved a couple of times quite a while ago, and he said that it wasn’t just sex. I’ve tried asking again but It always seems like the wrong time or I don’t know what to say; my friends all say I need to speak to him and I agree to an extent, but what if he says he doesn’t want a relationship with me? I’d rather live with the uncertainty right now than rejection. We’ve been “together” for a year now. I love him and I’m fairly certain he loves me. He takes care of me and is all round a sweetheart, I can’t even explain it’s just the way he is with me but I just don’t know what to do. He said to a mutual friend before we got together that he didn’t want to lose our friendship if something went wrong. I don’t know whether this could be a reason? He works all hours god sends and he was also cheated on in his last relationship. I feel like there’s a lot of reasons it could be, we’re only in our early twenties but he’s very mature considering what a lot of guys are like at this age. I don’t know what to think. Ladies, any ideas? Thank you!” – Toni

@CrazyJewishMom: Toni. Honey. I don’t care if his ex cheated on him on the middle of his family’s Thanksgiving dinner table! That’s not a reason to string you along for a year!

@KateFriedmanSiegel: Yeah, it’s time to DTR. It was time to DTR eight months ago.

@CrazyJewishMom: What’s DTR?

@KateFriedmanSiegel: Define the relationship.

@CrazyJewishMom: Oh, you’re so HIP, spawn. Please!

@KateFriedmanSiegel: It’s just a phrase, mother. Toni, at the end of the day, you’re not comfortable having things up in the air, and while I can empathize with being afraid of rejection, a year is extreme. You clearly have strong feelings for this guy, and the longer things go on like this, the more you’re going to be devastated if he’s not serious about you.

@CrazyJewishMom: Stop wasting time! Rip the band-aid off and have the conversation already!! DTR! Look at me, so hip. Toni, it doesn’t matter whether you’re 15 years old or 100 years old; you should never waste time on things that make you question your value and make you stress. That’s true whether it’s a partner, a career, anything! Your time is the most valuable thing you have. Don’t waste it.

@KateFriedmanSiegel: Yeah, and another thing to consider is that because you are young, this is a very formative time in terms of learning how to be in a relationship and setting expectations regarding what it means to be in love. I understand that you feel that this guy “takes care of you and is all around a sweetheart” but that is definitely not enough and not really true if you think about it. He’s certainly not taking care of you emotionally; he’s not making you feel safe and loved. You want proof? You have angsty conversations with your friends about feeling uncertain in the relationship, and you even felt the need to write us for advice! Love should mean feeling 100% secure in your relationship; a feeling of partnership. Yes, all relationships have stressful moments, but you guys haven’t even established a clear commitment which is just such a basic foundational element of being in a monogamous relationship. Are you even exclusive? All this angst and uncertainty is not fair for you.

@CrazyJewishMom: And by the way…the thing about him not wanting to get together because he worried about losing your friendship if something went wrong? Too late! You’ve been aboard the SS Manmeat for a year. That ship has sailed. And friendship can be a great foundation for a relationship!

@KateFriedmanSiegel: Bottom line: You deserve better than this uncertainty. You deserve someone who is so excited to be dating you that he’ll tell anyone who will listen that you’re his girlfriend! And if he isn’t that guy, better that you find this out now and move on to someone who values you and makes you feel safe, secure, and loved.

@CrazyJewishMom: Tell him you love him, and you want to be his girlfriend. If he doesn’t want that, NEITHER SHOULD YOU.

Want to ask us for advice? Submit YOUR question here! And did you know that @CrazyJewishMom is a licensed real estate agent at The Corcoran Group in New York? Let her help you find your dream home and with all of your real estate needs. Get in touch with her on her new Instagram account or send her an email at Kim.Friedman@corcoran.com!

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