[Jenbug20]

So there is this guy I met, he and I met about 3 years ago but nothing ever came of it romantically – we have been friends. Well his son moved in around the corner from my house, so he was over one day and asked if I wanted to go on a walk. So I went. First of all, he is going through a divorce. Second of all we have 25 years apart in our age. Anyway moral of the question is, he and I have been seeing each other for a little over a month now and I really, really like him. I know he has similar feelings but I am torn between telling him how I really feel or not. What should I do? Should I keep it to myself and let it be what it will be or just take the plunge?

[Ask April Masini]

Do not tell him how you feel. 😕 No good will come of it. It may make him feel pressured and/or it may make him feel like you stole his thunder because he wanted to be the one to tell you — men always like to chase and lead in relationships and when women take that opportunity away from them, the men feel less than great about the relationship. Instead, show him how you feel by flirting, being affectionate, and really enjoying the time you have together. 😉

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[Jenbug20]

Hi April, new guy new question.

So again, I am back. I met this guy (literally a week ago) he was introduced to me by my friend Ive known for about 3 years. It is her brother whom is 37 and I am going to be 26 (all too quickly). Anyway, he was in a long term relationship from what I have heard she broke it off with him. Anyway we hung out one night just casual playing dice at his sister (my friends) house. We stayed up until easily 1am just chatting and spending time together, we were laughing the entire time – great chemistry. The next morning we all decided to go hang out again ended up back at her house and we all watched a movie then I went home. He got my number. He text me Sunday and we were flirty back and forth. I responded to his text message he sent me late Sunday this morning and we began chatting again later today he basically asked me out again and when I say basically what he said was “I found this awesome spot above (insert name of city near where we live here) and I think we should go check it out” I said “Sounds great, Im down.” then we chatted a little back and forth and we both had to go because I had dinner plans and he was studying. He is a firefighter and also teaches at the local college. Anyway so I call his sister today because I have some stuff I wanted to drop off for her (clothes I borrowed) and we were arranging a time to meet up Friday to do that and she brought up the fact that she talked to her brother about me today and I asked oh what did he say and she said he told her that he was afraid to get into a serious relationship because there is a probability he might be moving out of the area and he did not want to hurt anyone. What do I do with this information? I dont want a screw buddy, not that he has at all implied that because he hasnt. I just dont know where to go from here….any advice? Do I ditch him or do I talk to him about this, I mean I am at a total loss?

[Ask April Masini]

Since he hasn’t asked you out yet, there’s nothing to do right now. But….if he he does ask you out on a second date, you can bring this up in conversation on that date and find out from him, directly, what’s going on, and if it’s even true. If he confirms that he is going away, then you can find out more and if the two of you aren’t compatible because he’s moving away, then you’ll know that then and you can move on. But wait to talk to see if there’s a second date before you bring it up, and then wait until you’re actually on the date to discuss it. 😉

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[Jenbug20]

Hi April, seriously – you are the best!
I talked with him last night over coffee. We are totally on the same page, there is no guarantee that he is moving and we both decided that if this (whatever this is) goes anywhere that will be a bridge we have to cross, if it happens, when we get there.
We had really great conversation last night we ended up talking for 3 hours. Anyway…I know his funds are tight right now because he is in school full time and doesnt start working again until late August. So my question is, he has not asked me out technically yet. I mean he brought up going to that spot up north but nothing is set in stone yet. My family is in from another country and they’re having a barbecue Saturday and I was tempted to ask if he wanted to come with me and hang out, swim, etc. with my family. Should I ask him this or just wait until he asks me out?

[Ask April Masini]

You should wait. I know you want to go out with, but don’t take away his opportunity to ask you out. Men really want to chase after a woman and win her over, and when you take that away from them by making the first move — even by inviting him to a party, it’s depriving him of that choice to ask YOU out first.

And just because he doesn’t have a lot of money doesn’t mean he can’t ask you out to do something that’s not expensive (like coffee or ice cream) or free (a walk on the beach or a picnic in the park).

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[Jenbug20]

You are always right.

I didnt ask him out he actually offered to come over and help me with a couple things, so I said yes. Hes coming over tonight and bringing dinner 🙂 I WILL NOT SLEEP WITH HIM hahaha Things are super casual between us but really good. I guess I just need to stop second guessing myself so much and go with the flow. He called me last night for no reason at all and we ended up talking on the phone for a couple hours. Men don’t normally talk on the phone right? Is there any chance he could just be acting nice to get in my pants? See there I go, second guessing my gut again but I am notorious for reading signs the wrong way and jumping in too quickly.

[Ask April Masini]

He likes you! He called because he’s interested in you — and he’s bringing dinner over because this is a date. Do your part by looking great, smelling great, flirting with him, and giving him something to chase.

Very happy for you! 😀 Try to relax and not jump the gun. Get to know him, and see if he is someone you want to continue to date. 😉 And do not make the first move or ask him out or invite him over for a second get together — let him make those moves. 😉

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[Jenbug20]

YAY! I was praying you would say that haha

At what time would it be appropriate to ask him out or to hang out with my friends at a BBQ or some other similar type of event?

[Ask April Masini]

For now, stop thinking about asking him to do anything. You have a tendency to jump the gun — and that will get you into trouble. Instead, focus on dating him and seeing who he is and who you are with him. 😉 Don’t even schedule into your calendar a time to ask him to do something with your friends. It’s too soon.

[Jenbug20]

Thank you. I will get it out of my head and just let it be. I know better than this…. ❗

[Ask April Masini]

You’re very welcome. 😀

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[Jenbug20]

Hi April,

Back so soon you ask? Yeah. Im that silly.
Anyway, we spent all weekend together. We did sleep together but I mean literally that – sleep. we did not have sex. Anyway He stayed the night Friday, Saturday and Sunday night at my place and we just hung out watched movies, went on a walk, hung out, nothing extravagant. But it was fun. He met my daughter not in a serious manner just casual which he seemed to take to her very well and she to him. My question here is, I would presume he likes me…yeah? His birthday is in 2 weeks and I have no idea what to do. He had mentioned wanting to go to the beach before school starts (he is in school for his masters so he will be busy when that starts) so I was thinking maybe asking him if he wanted to go away for a night for his birthday? Would that be weird? I don’t have any other ideas. Also, in your opinion what classifies a “committed” relationship? I am just not sure where to go from here. I dont know why I make things more difficult than they are.

Thanks in advance for your help, as always 🙂

[Ask April Masini]

Here’s the time line you should follow: For the first three months that you’re dating, you should decide whether you want to continue dating him, and play the field. Especially since you’re a single mother, you need to focus on whether he’s going to be a good step-father and husband, since I assume you’re looking towards marriage as a relationship goal. Pay attention to who he is, who you are, and you are together. You should also assume that he’s dating other people, too during this time — so you don’t fool yourself into thinking the relationship is something it’s not. So for you, since you met him in mid-July, you should continue to consider this casual dating until about mid-October. If you’re both still together then, and things are going well, you should spend the next three months deciding if you want to be monogamous. So around January is when you should decide if you’re serious with each other or not. That’s the point when you start getting monogamous. 😉

As for his birthday in two weeks, you should definitely NOT take him on an overnight. It’s way too soon for that type of commitment. Instead, get him something nice in the $50-$100 dollar range, depending on your budget. Or you can make him a nice dinner if your daughter is with her father that night.

I hope that helps!

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[Ethan Morales]

Cut through the noise: you’re dealing with two different problems that look similar availability and intention. In the first story there’s a big age gap and he’s mid-divorce; in the second he’s potentially moving and afraid to commit. Both situations create built-in obstacles to a stable relationship. That doesn’t mean attraction can’t exist, but it does mean you need to treat signals from them as complicated signals, not straightforward interest.

Don’t hand over your feelings as a solution. Telling someone “I really like you” hoping it will fix ambiguity rarely works. It can put pressure on them, make them recoil, or make them feel like you’re asking them to choose before they’re ready. Instead, show consistent interest without begging for promises laugh, flirt, touch, make plans, and let them respond.

Watch for follow-through, not theatrics. If he’s into you, he’ll make time, ask to see you again, and check in. If the pattern is kiss-goodbye-and-ghost or vague plans that never land, treat that as information: he’s not ready or not serious. Kissing and chemistry are nice, but consistency is the currency of dating worth investing in.

Be clear about what you want privately, to yourself first. If you’re looking for a relationship that could go somewhere, decide how long you’ll tolerate ambiguity. If you’re open to something casual for now, fine own that. But if you want commitment, say so in a low-pressure way when the moment is appropriate: “I like this and I’m looking for something real. Are you?” Short. Honest. No drama.

Don’t waste time on what-ifs. If he’s moving or emotionally unavailable (divorce recovery, younger-younger dynamic, fear of commitment), those are logistical and emotional roadblocks you can’t fix for him. You can be kind, present, and clear but don’t pause your life waiting for someone to catch up. People who want to be with you will make the case with actions.

Keep seeing him if the chemistry is good, but don’t escalate emotionally until you see reliable behavior. If a second or third date lands and he’s still hedging about the future, ask the one direct question that gives you clarity: “Where do you see this going?” If he dodges, move on. If you want, I’ll write you a short, no-pressure line to say that lets you get an honest answer without sounding desperate. Which do you want the “soft signal” text or the “straight-up” question?

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