[April Masini, your AskApril]

The biggest piece of advice I can give you is to use a timeline I recommend for dating: The first three months of dating anyone should be with the goal of simply finding out if you want to continue dating each other. And, you should assume he’s playing the field, as you should be as well. What this does is put your focus on learning about each other and really getting to know each other and yourselves. If, at the end of three months, you want to continue dating, you should use the next three months to decide if you want to be monogamous. Again, this takes the pressure off the relationship and lets you focus on getting to know each other. What you’ve learned in the three months you did date him is that he either wasn’t honest with you about playing the field, which he was doing, or that he realized he just wasn’t into you — and he jumped the gun on committing to you which may have seemed romantic in the moment, but wasn’t a good move for the long run. Dating smart means slowing things down and really getting to know each other.

The reason he’s contacting you now is because he may want more of the same, and because you didn’t blow up his phone he thinks you’re okay with his behavior. If you do decide to date him again, make it clear that you’re not interested in a commitment to him until you get to know him a lot better, and do keep your other options open since he probably is, as well.

I hope that helps! 🙂

[April Masini, your AskApril]

Moving in together was a big step! But it sounds like you have some reservations about the relationship now that you’re living together. And, you’re right — your second thoughts may have to do with your suddenly sharing living space and not having your bachelor life which you miss sometimes, but it may also have to do with your simply not being ready for this type of commitment. Living together is a big deal — maybe more of a big deal than you imagined. Lots of 28 year old men, like you, don’t feel ready for the next step. You’re not alone. But, that said if you do break up with your girlfriend over these reasons, she will probably move on. She’s invested four years in the relationship and she’s moved in with you — a big deal for her as well — so make sure that asking her to move out — or your moving out — is really something you want before doing it. As for the ex-girlfriend you’re interested in again, remember that there are no guarantees, so if you want to date her, you should — but be open minded that this may or may not work out. You don’t have to do anything today — you can let this pay out, but do be mindful of your feelings and if you discover that you really did make a mistake, then move to correct it so neither one of you wastes time. 😉

[April Masini, your AskApril]

Dating is competitive, and when you use a dating app like Tinder, you’re putting yourself smack in the middle of high competition. So if you hate dating — which I think really means you hate competing — look for dates in places where competition is less intense. Like real life! Your coffee shop, your gym, your apartment building, your supermarket — these are all places to start up small talk and introduce yourself.

That said, it sounds like you had one coffee date with this woman and then she met someone else she’s dating now. My advice is to definitely not give up — but you have to change your tactic. Texting hasn’t yielded you good results. Send her a gift with an enticing note that you miss her. Don’t beg for a date, but do let her know what she’s missing with your generosity and your commitment to chasing her. (Yes, you can chase her!) And at the same time, play the field. You have to balance the chase for this woman with looking elsewhere as well. And if that sounds overwhelming, dial it down, and simply smile at 20 new women each day — and if they smile back, compliment them and see if conversation begins.

Do chase — but don’t give up on the rest of the women out there!

[April Masini, your AskApril]

I don’t think your ideas are creepy at all — but that’s me. Everyone is different. Why not accept her invitation and bring her flowers on the date. If it goes well, then ask her for her number at that point because if she’s willing to ask you out and take you on a date, she should be willing to give you her phone number! And when she gives you her number, you get the ball rolling by taking the lead at that point. Hope that helps! 🙂

[April Masini, your AskApril]

Yes! He likes you! 🙂

[April Masini, your AskApril]

It’s WAY TOO SOON for you to have “the talk” about where the relationship is going. You mentioned six dates — but you didn’t say how long you’ve been seeing him, so here’s a great rule to use (because it works): Use the first three months of dating to get to know each other and simply decide if you want to continue dating. Assume he’s playing the field, as you should be too. If you continue, then use the second three months to decide if you want to be monogamous. After dating for six months you’ll know a lot more about him than you will in six dates. 😉 And because you have a 4 year old child, it’s really important that you date smart and find someone who’s not just a great partner for you, but a great potential step-father or step-father figure for them. So, slow down!

Next, don’t ever initiate the talk. Guys hate it, and it makes them feel backed into a corner and pressured. If they want you and they want to keep you for themselves, you’ll know it because they’ll act like it and they’ll even initiate it. But when you bring up “what are workings towards,” this 27 year old guy is going to feel like you want a commitment he hasn’t offered or possibly thought about yet. It may also make you look desperate, which isn’t attractive — and you may not be. 😕

I hope that helps.

[April Masini, your AskApril]

I think you should move on. It sounds like you really like him, but he’s just not interested. If he were interested, you’d know it because he’d be more assertive about it. Why not focus on the guys around you and find someone who’s local and interested enough to ask you out? Dating is great because the way you really know that someone is interested is when they invite you on a date. It cuts out the guess work. I’m sorry you’re disappointed, but I think that you’ll find someone great who is interested and does want to date you. 😉

[April Masini, your AskApril]

She does like you! And because you’re both teenagers and not experienced at dating, she’s wanting to make it a group date so she can feel more secure as she gets to know you. I think you’re doing everything right! 🙂

[April Masini, your AskApril]

Trust your instincts. It sounds like he’s having an affair with his ex-girlfriend. Since you’ve been together for 12 years and have a 4 year old child together, you have a lot invested. The important thing to remember is that cheating doesn’t happen in a vacuum. It’s very easy to point fingers and blame someone, but this isn’t a person who is a chronic liar. He’s someone who decided to go outside your relationship to feel good about himself. The question for you is, what was he getting from his extracurricular romance that he wasn’t getting at home, and if you can answer that, you’ll find a way to heal the relationship. Sexual betrayal is very devastating, but it’s not always the end of the relationship. Open communication and talk to him about why he went to her and what he gets there… and then, if he wants to make things work with you, figure out where the two of you can begin to heal. 😉 I hope that helps. Let me know how things go.

[April Masini, your AskApril]

Your experience seems unique. 😉

[April Masini, your AskApril]

You’ve been together for 3 years, but married for 18 months, and your child is 18 months old, so I’m guessing you got married because you were pregnant or you got married and got pregnant right away. In either case, that means you didn’t have a lot of time to explore marriage before adding in a child — and [i]any[/i] family with a new marriage and a new baby or toddler is going to be under duress. It’s very normal. The problems you’re talking about can be addressed and even overcome, but only if you’re both willing to do some work. Not all the work, but some — you have to be willing to meet at a middle ground and you have to want the same outcome.

Here are a few tips: 1) Have sex. You’re probably both doing so many things for others (the baby, the bank with your mortgage, your careers) that you don’t have time for the relationship. Plan sex. Have it even if you don’t feel like it. Get a babysitter, enlist Grandma — and have a glass of wine or two with a nice, easy dinner and a bubble bath with candles and have sex. You’ll both feel better about the relationship and yourselves. Sex is important in marriage and it’s an easy fix if you’re committed to it. 2) Give your spouse one compliment a day and make it a doozy! Tell him how awesome he is in bed, or how you forget how truly handsome he is. Make him feel good about the relationship and himself in it. It will prove contagious — I promise. 3) Show affection outside of the bedroom. Hold his hand. Hug him in the kitchen. Touch him affectionately because he’s a good person and you love him. And TELL HIM you love him.

These are 3 cheap, easy and effective ways to get things back on track. Try them — and let me know how it goes.

[April Masini, your AskApril]

I’m sure she has feelings for you, but they’re probably not romantic. The two of you dated, broke up, and you moved out. Now, she’s got a new boyfriend and you’re her son’s babysitter. That doesn’t mean you shouldn’t try and win her over and get her back. 😉 Rather than tell her how you feel, show her. Buy her flowers. Invite her to have coffee. If things seem to go well, then ask her on a date. Be careful not to badmouth the current boyfriend — it’s going to look like you’re bitter and it may jeopardize your relationship with her. Instead, bring your A game and promote yourself. And use the knowledge you have from your relationship of 8 months with her — you mentioned she fell out of love before breaking up and moving out. Figure out what your part in that rift was. Did things get boring? Did you take her for granted? Was there something that was missing or that you can bring to the table now, that will show her that her prior concerns are no longer relevant?

Hope that helps!

[April Masini, your AskApril]

I know that this feels like he’s in the wrong, but the reality is you’re making choices that aren’t right for you — and trying to blame him. If your 35 year old fiancee has a history of quitting jobs because he doesn’t like them, then you have to understand that by lending him money, you’re enabling his behavior. You were probably trying to be nice and supportive, but when a grown man quits a series of jobs and borrows from his 25 year old fiancee, he’s not someone who’s interested in being stable or financially supporting a relationship or a marriage. The bigger problem is that you’re trying to believe he’s someone he’s not. 😳

I can hear your frustration and your fear of asking him about this issue directly — because you’re going to hear answers you don’t like. At a certain point you’ll decide that knowledge is more important than preserving the fantasy you’re desperately holding onto. I hope it’s soon, for your sake. The reality is that you’re engaged to marry a man who isn’t stable and isn’t interested in being stable. It doesn’t sound like this is who you want to marry, but you are upset about the idea of leaving because you’re not compatible. I think the writing is on the wall — this problem isn’t going to get better. This is who he is. Ball is in your court. Stay and face reality, or go and find a man who is more compatible with your values.

[April Masini, your AskApril]

You’ve only been dating for four months, so you’re still getting to know each other. The death of his childhood friend is a big deal, and it may affect him differently at different times. It sounds like you’ve offered to be there if he needs to talk, and there’s not a whole lot else you can do except to be sympathetic and understanding of the situation. Overall, it sounds like you’re trying to rush the relationship you’re in with him, and you can’t do that — because it won’t work. Try to relax into the fact that it’s only been four months of dating so far and you have to let the relationship find it’s own way. Typically, I suggest that you wait until six months of dating to decide if you want to be monogamous because that gives you time to really get to know each other. It sounds like in the four months you’ve been dating, you’ve seen some events and behaviors from him that inform your relationship. The way he handles the death of a friend, a relationship with an ex and a job crisis are all very important pieces of information for you to use to decide if this is someone you’re compatible with for a long-term relationship. Stay the course, relax and be there, but don’t try and force things. 😉

[April Masini, your AskApril]

You did do the right thing. I think you really understand what the friend zone is, and that you don’t want to be in — which is wise. He’s all over the map, saying he wants to be friends, then trying to kiss you; dating you then breaking up and seeing his ex…. he’s making it very clear that he’s not boyfriend material right now. So, rather than end this on a bad note, tell him that you like him way to much to be anything but a date and possible girlfriend and if and when he’s ready for the the real deal, to call you for a date, but otherwise, you wish him well. It shows you value yourself and your time, and it keeps things upbeat while setting boundaries. 😉

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