How To Ask What He's Looking For Without Initiating The Talk?

Hi Miss.

Can I ask what you talk about on all these dates? Usually the guy who’s ready or wanting a relationship with a lady will bring that topic up pretty early to suss out where the woman’s at.

The best way to bring it up is to ask in an inquiring manner such as “what is your five year plan?” “I’m curious, what do you think about marriage?” “If you were to have kids how many would you want?” Wording it this way doesn’t put him on guard but allows for a good way to open up the dialogue between the two of you.

One of the best marriages I know is a couple who dated other for three years (one year was the engagement) and during those three years they literally “planned their marriage” by asking those questions “what if blank happens” and they would come up with a SOLUTION so when that event happened they either deferred to what they had already agreed to and stuck to it or come up with a solution because they had learned the “art of negotiation” so well that problem solving came easy to them. They’ve been married over 60 years now.

Honestly, I would bring it up that you are looking for a serious relationship. If he gets scared off by that or just falls off the face of the earth, then take that as a blessing in disguise. You withholding that you want more out of this arrangement is not going to get you what you want. It’s just going to cause you to get more invested, feelings are going to grow deeper, and if you find out later he doesn’t want what you want you’re going to feel more devastated, and a lot of precious time was wasted. Go ahead and tell him what you want. The worst case scenario is that he doesn’t want a relationship and that’s ok. It’s not the end of the world and there’s plenty of men out there who do want a relationship. You’re only 26. You’re still young and have plenty of time to find Mr. Right.

I like your proposed question. Also, if a man is looking for the same thing as you, he would not get scared or runaway. Since I’ve learned so much from this site and from reading articles here and other dating books, when I decided to go back out there to date, I wanted to be very upfront that I would only meet those who want the same thing I want, i.e., an exclusive, committed, long-term relationship. Exactly these words because I want to be super clear. Btw, I widowed with 1 child. When I met my boyfriend (now), I asked him on our first date what he’s looking for. I’m 49 and had been married so I could care less if he got scared when I asked. I don’t have time to waste my time with the wrong match.

Thanks for the responses! I appreciate all of the advice given.

Lane, to answer your question, the topics of marriage and kids have come up in conversation. He said he’d want one or two kids. He says it’s sad that some people he knows got married just to have a wedding, and that marriage should be so much more than that.

We have discussed dynamics in our parents’ marriages, and factors that make two people a good match for each other long-term. He did say early on that he wasn’t looking for just a hookup. I said I wasn’t, either. And at one point he mentioned his “future wife”…

Somehow we’d started talking about this silly, hypothetical idea of driving to Boston for a date (it’s silly because we live 400 miles from Boston). He commented: “No way would I do that, unless it’s to meet my future wife or something.” Then literally in the same breath, he said, “I’d drive to Boston with you for a date if you wanted to.” And I fully believe he meant it.

At this point, we’ve danced around and around the topic but I’ve got to just ask him. I want to give it a few more weeks and see if he brings it up. There’s a chance he could initiate the talk, and I’d get my answer without having to ask. However, if still nothing in a few weeks, I will say something for sure.

Update and Need Help!!! Be brutal if you must. I may need a slap in the face.

This past Saturday, we had “the talk” and we’re now official. Here’s how it went down:

Me: I’m just curious since we hadn’t talked about it… Are you dating anyone else?
Him: I’m not.
Me: I’m not, either.
Him: Actually, there’s something I’ve been wondering … you don’t have to answer right away. But I’ve been wondering whether we’re an official couple.
Me: Is that something you want?
Him: Yes. I feel a strong attraction and connection to you, and I want to be in a relationship with you to deepen that connection.
Me: I feel the same way, and I want that, too.
Me: So just to clarify – you’re talking about being boyfriend and girlfriend, correct?
Him: Yes. I’m excited that I get to be your boyfriend!

So that night, we had a great time together BUT the next day, I freaked out! All of a sudden I felt anxious and needy. All of a sudden I got upset since I wouldn’t see him again for a week. WTF?

We established a communication pattern before we were official, where we did NOT talk every day, and I was totally cool with that. Usually we’d both take an hour or so to respond to each text because we’re both quite busy. I was totally cool with that. Plus, we’d talk on the phone typically twice a week, and that hasn’t changed. But now that we’re official, I’m freaking out (internally) and I don’t know why! I spent most of Sunday feeling depressed – even though we did text each other a few times. I’m not sure why my whole mindset seems to have changed for the worse :(

Why am I feeling so vulnerable and needy? I do have a lot going on to keep my time occupied, but still. Whenever I get a free moment I find myself feeling anxious about the relationship. It’s not like I think he’ll cheat on me – I do trust him – I just miss him a lot when we’re not together. I’m at a loss here. Help?

Well first let me say….good for you that the talk went so well and he picked up the ball and ran with it for you!! Yay!! But I think what you’re experiencing is exactly what guys worry about and why they drag their feet on giving the official “title” of girlfriend. As soon as you establish that, you are creating EXPECTATIONS on both sides.

And apparently your expectation is that now your communication should increase. So when it didn’t you got anxious. There are little nuances of the relationship that have now shifted and both of you have to figure out what is expected of you in your “new role” so to speak. Things with my boyfriend did change once we became exclusive and official. There was the expectation that we would be doing things together on the weekends and we would check in with each other when making plans with others. There was the shift to daily phone calls and not just texts. There was the checking in with each other to say where we were going or what we were doing. There was more of a sharing of things that were going on throughout our day. It wasn’t all at once but kind of a gradual move in that direction.

So personally I do think things should change a little now that you’re official. Maybe you should initiate more communication with him if that is what you want and see how he responds. But don’t let it come from a place of being needy. Just send a fun little flirty text saying ” thinking about my amazing boyfriend and missing him.” Something that will make him smile. But don’t expect a certain response or need him to respond in a certain way.

Don’t forget..you got exactly the result you wanted here. Sometimes when things are going great it’s natural to get this feeling of anxiety worrying that things can’s always be this great. But that should just be a fleeting thought and not something you allow to get in your head and make you anxious. You should be able to push it out of your mind, enjoy your moments together and appreciate what you have.

Thank you all so much for your responses! This makes a LOT of sense. My expectations shifted and I didn’t even realize it. It’s like the moment he said he wanted to be in a relationship with me, I got more attached and wanted to keep him closer to me. But, I know smothering a man is bad news, haha. I’ll just keep being calm and cool, and happy when I see him because I truly do enjoy being with him.

Throughout the past week, I’ve initiated conversations a bit more than before, but not too much. Like I’ll text him a picture of my dog in a funny outfit, and my bf will respond and then he’ll take the ball and keep the conversation going. The other night I called him with a resume-related question (I’m job hunting and asked for his input on how to word something on my resume) and we chatted for 45 minutes. Usually he initiates calls, so I figured I can call him sometimes, too.

I really appreciate all of your advice above! I haven’t been in a relationship in a long time, and arguably, I’ve never been in a HEALTHY relationship. This is new and scary but really awesome. We have a double date tonight, so I’ll keep repeating to myself: “Happy girlfriend, good. Psycho girlfriend, bad.”

Thanks, PJC! I appreciate the kind words, and I wish you the best with your guy! Just take it one day at a time and don’t let your thoughts run away from the present – easier said than done, haha