[April Masini, your AskApril]

I don’t think she’s going to give you a chance without seeing some change. And it can’t be talk. It has to be action. I’m not suggesting you pick up and move to her country to show her you mean business. But I do think you need to extend some gestures — send her flowers, send her poems, send her framed photographs of the two of you, send her a gift certificate for a massage at a spa. And if possible, whisk her away for a romantic weekend. You have to show her the side of you that she never saw and give her a reason for wanting to get back with you. Since she’s a lawyer, she has an analytical way of thinking and she’s going to need convincing. You can’t just tell her what you did wrong and what you will do right. You have to show her what you ARE doing right. This is going to require behavior modification on your part. Ball’s in your court. Show her your A game.

[April Masini, your AskApril]

Don’t tell her how you feel. It’s just going to make things awkward. If you want to date her, then date her. [i]And[/i] if you want to date her, you’re not her friend. You’re either in the friend zone, or you’re someone who wants to compete to win her over. The problem is you’re trying to play both sides of the coin, being her friend (which you’re not) and being a guy who dates her. My advice is to understand she’s only just started seeing someone else, so she’s fair game. If you can win her over, then go for it! 😉

[April Masini, your AskApril]

If you really have no intention of getting back together, then don’t contact him. A clean break means exactly that — a clean break. 😉

[April Masini, your AskApril]

Don’t give up, but don’t put all your eggs in one basket. 😉 For whatever reason, he’s dragging his feet. He may be someone who flirts like this with lots of women. He may have a girlfriend. He may be scared to ask you out. Who knows? And it’s not your guess. Instead, play the field and distract yourself with other guys, other personal interests, and other ways to let him know you’re really keen on him, but you’re not sitting around waiting for him. 😉 Give him something to chase after and if he does, great. If he doesn’t — his loss. Next! 😀

[April Masini, your AskApril]

Don’t give him an ultimatum. That’s always a mistake. Instead, decide if this is a deal breaker for you or not. If it is, then move on. If it isn’t, find a way to be okay with the the fact that your boyfriend has these social and family differences. The ball is really in your court, not his. If you give him an ultimatum you’re just going to stir the pot and create more fighting.

I don’t know how old you are or if you’re thinking about marriage, but if you are considering marriage and kids, consider the consequences of his behavior on future children. If one of them has a birthday party, how will you celebrate it and how will you handle family? What about a wedding? A shower? Funerals? If you’re okay going to these things without him, and having your kids go to Thanksgiving, Easter or other family get togethers without him, then you’ve got a future together. If you can’t see that happening then you may be looking at a relationship deal breaker.

You’ve got some tough questions to ask yourself and to answer, but it’s time. If you do want to have a conversation with him, stay away from ultimatums, but do ask him about how he wants the two of you to handle things if you have children together and there is a family Christmas or a cousin’s birthday party for the kids. Since you’ve been dating for three years now, the question isn’t inappropriate. 😉

[April Masini, your AskApril]

Two things:

First: You’re in a friend zone type of relationship with him, only it’s not friends, it’s colleagues. You’re in the work colleague-zone. To get out of it, you have to flirt with him and show him that you’re interested in a relationship beyond what you have. You’re absolutely right not to have a conversation about your feelings. That’s just awkward and will make him feel pressured if he’s not sure or not ready. Instead, flirt. Smile, joke, compliment and ask questions of him about things outside of work — for instance, ask him about a restaurant, a neighborhood, a band, his family, college friends — any of these topics which will turn conversation towards the social and personal, and not work.

Second: Since you’re his superior, you have to be extremely careful to not put yourself in a position where your interest is seen as sexually harassing. This is the power dynamic where law suits start. Keep your interest as much outside of the office as possible, and don’t pressure him ever or trade promotions or work favors for social ones — or even allow the perception of such.

Hope that helps! 😉

[April Masini, your AskApril]

Definitely flirt with him. Flirting is the way you can show him, without telling him, that you’re interested. It’s a lot less awkward than telling him because it’s lighter. It’s all about smiling at him (a lot), laughing at his jokes, complimenting him, asking him questions about things — and basically showing him that you’re interested and you think he’s great. He’ll notice you, believe me! If he’s interested, he’ll respond with interest and even mutual flirting. Then, the ball’s in his court to invite you to do something together.

Hope that helps! 🙂

[April Masini, your AskApril]

I understand your fear of rejection. It’s very common. You’re afraid of things not working out and losing contact with her. But I can tell you what’s worse than rejection: regret. If you lose her because you never get a shot, and she was the one, you’ll feel a lot worse than you do because you’re afraid of rejection or things not working out. Let that be your motivation.

Get out of the friend zone and be the guy. Your’e the one who’s responsible for asking her out, making the first moves and leading. She may be anxious because she sees your reticence to invite her out on a date or initiate sex. This may make her think you’re just going along and are not that into her, in spite of your having a great time. From her point of view, you’re not taking the lead — and that’s probably from your point of view, as well. Your taking the lead is what will send her the message that you’re in. Be careful to behave in a way that reflects your intention.

Hope that helps! 🙂

[April Masini, your AskApril]

The simple answer is: Don’t. Don’t talk to him about the status of your relationship. You already know it. You just don’t like it. 😉 The two of you are hook up buddies. That’s it. He was ready and you were willing.

Bringing up the relationship status, which you both already know, will appear needy, and besides, guys HATE “the talk”.

Let me know if you have any other questions. 😉

[April Masini, your AskApril]

It doesn’t sound like this woman is into you, or you into her — and the fact that you met her because she was cheating on her boyfriend with you, wasn’t a good sign for a healthy future. 😕 So you shouldn’t marry her. And if you’re living together, you should move out. She’s in love with her ex. Not you.

As for your concern for the kids, since you’re about to have a third without any marriage involved, be single. Don’t date. Just focus on being a dad. Set up a custody schedule for all three kids, so you have scheduled time with them. This will make them feel less anxious about the your not living with them. And really — take a break from dating for a while and focus on the children you’ve fathered.

And if you don’t take that advice, at the very least, get some birth control and use it. If you keep having children with women you’re uncertain of, you’re definitely going to create chaos.

Hope that helps.

[April Masini, your AskApril]

I’d love to answer your question, but first… please repost as a “reply” to the string of posts you’ve already started on this site here: . It’s easier for me, and anyone else here who wants to weigh in, to see your entire string of posts in one place. I’ll look out for the repost and answer you there. 🙂

[April Masini, your AskApril]

Decide what you want. 😉 Do you want to get married? Live together? Date from different homes? Are you looking for someone who’s financially compatible enough to travel and enjoy entertainment that requires a particular budget? And if so, is that a deal breaker for you? (It sounds like it might be, but you haven’t spent enough time deciding the answer.) If you want to remarry, there are some obvious issues here and possible deal breakers. If you want to date, then you can do so — but he won’t be able to travel as you will. If you want to play the field a little longer and see if there’s anyone out there who’s better matched to you, then you should do so. Since I don’t hear a ticking clock in your questions, take your time and figure out what you want, and when you do, if he fits the bill. Just because he’s in love with you doesn’t mean you’re a match. And just because you’re incompatible for marriage doesn’t mean you can’t see each other monthly while you play the field.

[April Masini, your AskApril]

Your age difference isn’t the issue here. It’s the fact that you moved in with him before dating him. That’s a tough goal to make work at any age! Usually you shouldn’t move in with someone before knowing him really well (dating for a year), because if things don’t work out, it’s a lot more traumatic to break up than if you’re just dating from your own homes. The other problem is that it sounds like you moved in with him because you had family troubles and no where else to go. 😕 I’d normally suggest you work out your family troubles, or move into your own place with roommates before you move in with a guy you haven’t dated.

But since you’re already living together, you’re getting to know each other. You have to decide if you want to make this work or not because I’m not hearing any real deal breakers here — just differences. If you can compromise on the differences, you may be able to make this work, but if there’s too big a gap between you both, obviously, you’re going to be in for a tough ride if you stay.

I hope that helps.

[April Masini, your AskApril]

When someone stands you up, after you’ve been dating for four months, they’re being rude, disrespectful and troubled. Do you really want to date someone who has those three very unattractive qualities? My advice is to move on. Either she’s not interested, or she is interested and she’s disrespectful.

[April Masini, your AskApril]

Thank you.

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