Ask A Guy

The Ask a Guy columnist is here to provide a guy's opinion on any questions needing a male perspective. Whether you want to know how to ask a guy to a dance, ask a guy out, or just need some masculine insight to your current relationship, this is the place for you to decipher the male psyche!

He Needs Reassurance (And Honesty)

I've been dating a guy for about three weeks now and he asked me (in person) the question, "how long do you think our relationship will last?" I said I didn't want to think about it. He said good answer. Then I asked him the same question and he said he thought I was going to dump him when he goes away for college. (He's a senior and I'm a junior.) I realize he thinks this because of some things I've said, but I never meant them that way. I tried to convince him of that but he still thinks it (he admitted that and I can tell it bothers him).

Background info:

  • we were friends for a long time before dating
  • we both liked each other for a long time before dating but neither of us said anything
  • the reason we're dating is because I asked him to prom
  • we get along great and have a very open and honest relationship so far
What I'd like to know is:
  • Why would he ask me that so early in the relationship?
  • How can I prove to him that I'm not planning on dumping him when he leaves?
I really, really like this guy, and even though it's only been a few weeks, the thought of not being with him really depresses me. I need some help. Thanks for your time!

earnest | age 17 | March 15, 2010

Daniel says...

Plain and simple, this guy is asking this question because he really likes you. He likes you enough that he is already dreading the possible end of the relationship. Simply put, he's in that phase of the relationship where he isn't quite confident enough (because he doesn't know you well enough) to trust what the two of you have. All he knows is what he feels and he is intimidated that he feels so strongly without knowing exactly how you feel.

The key to effectively reassuring this guy is to be completely honest with him. In this case, honesty is not telling him you aren't going to break up with him when you he goes away for college. You just can't make that promise; it sounds flimsy, forced, fake, and unreliable. As much as you may not intend to break up with him when he goes away for college, he's probably still something like five months away from leaving. That's almost seven times longer than the two of you have been dating! You don't know how you'll feel in August or September and it's hard to tell how he will feel, too.

What you should tell him is how much you like him. Tell him how happy you are when you are with him and that you really want to try to make a long distance relationship work while he is at college. Put some of the burden on him by saying that you want this if he is willing to work with you on it - a burden shared is a burden halved. By doing so, you will help him to feel more invested in the relationship and less like he is just an over-emotional teenage guy who doesn't know what is going to happen. Saying you want this if he is willing will reinforce his feelings and let him know that you are feeling the same way he is.

Remember that long distance relationships take a lot of work, but they can also be very rewarding. You can't promise that things are going to work out, but you certainly want to give it a try. He needs to know this and not some fluff about how you'll never leave him.

Tags: ask a guy, advice, relationships, communication, long distance relationships, honesty

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Tag - You’re It!

I really like this guy, and I want to go out with him more than anything. My friends say he talks about me all the time (in a good way) because my friends have class with him, too. When the two of us are together, apparently we play eye tag with each other. I have never asked a guy out before in my life (I usually get asked out), so I can't tell if I should ask him out. I need your opinion- should I ask him out, or should I just wait until he asks me out?

FlippingConfused | age 19 | March 15, 2010

Daniel says...

It sounds like you don't know this guy well enough to be able to tell whether or not you should ask him out. By that I don't mean that you can't tell whether or not he likes you, because he clearly does. What I mean is that it's hard to tell what this guy's preference would be. The two of you don't know one another all that well and it's entirely possible that he would prefer to be the one to make a move first. Some guys have a personality that causes them to lose interest when they are pursued by a girl and, as a result, would prefer to be the one to make the first move or ask the girl out on the first "real" date.

This should not prevent you from getting to know him better. Talk to him during school, sit next to him if you see him at a sporting event or other extracurricular activity, and even invite him to hang out with your friends if you're having a get together. The key is to become friendly with him and to flirt when you have the chance. Doing this will indicate to him (in a fairly subtle way) that you are interested and will encourage him to pursue something more.

If you try this for a while and he still seems unwilling or unable to make a move, then it may be worth throwing caution to the wind and actually asking him out on a date. If it seems, after much effort, that he is unwilling to make a move, then you don't have anything to lose by making one yourself.

Tags: ask a guy, advice, relationships, flirting, gauging interest, pursuing a guy

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Dating Again

This guy and I dated in December and broke up in January. We still remained really close and we are really good friends now because we are so much alike. Now it's gotten to where he calls me every now and then but every time we hang out now he always will kiss me goodbye. Does him kissing me mean anything? Or is it just because we are so close?

tellie123 | age 21 | March 14, 2010

Daniel says...

Guys kissing a girl goodbye is one thing when the girl initiates a friendly kiss on the cheek. But when a guy initiates the kiss with the girl he's either gay, European, or interested in dating you. Given that you dated already, it's safe to say that gay is out. Your manner of speech doesn't indicate a propensity for British English, so I assume European is also out. That leaves "interested in dating you." He is calling you on occasion, but it sounds like he is probably trying to take things slowly and see where they go. He may even be intimidated at the thought of asking you out due to your past relationship. Hey may be worried about making a move too quickly out of fear that you don't really want to give things another try.

If the possibility of dating again does present itself, remember that you need to be careful not to make the same mistakes and fall into the same behaviors that caused your relationship to break down the first time you dated. When we are with someone we know, it is human nature to fall into known behavior. Why do you think so many second-chance relationships fail? It's because we all have certain behaviors and certain expectations that are "automatic"; often we have no control over the actions and don't even realize we're doing them. Spend some time assessing what happened the last time you dated. Why did you break up? What could have been done differently? Remember that even if it was something that he did to end the relationship, there were likely some behaviors you did to contribute to it.

Even if you don't wind up dating this guy again, this assessment will be useful for you to apply to future relationships. The best thing we can do is be ready when that next person comes along for us.

Tags: ask a guy, advice, relationships, dating, second chances, what went wrong

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You Stay Classy, San Diego

I recently stopped dating somebody (actually they stopped dating me!), so I'm trying to move on. This guy who I've known for a little while asked me out and even though I've NEVER kissed on a first date before, I ended up making out with this guy. Mainly because he just went in for the kill and I played along. I liked the attention A LOT, but I want to remain classy and stick to my values. I also want to see this guy again, and he wants to see me. So, basically what I'm asking is: how do I tell him to take it slower without it being awkward or embarrassing on his part? I don't really know how to approach the subject and am not sure what to say. How can I not seem uptight but retain my values?

4sure86 | age 19 | March 14, 2010

Daniel says...

Your problem is not uncommon - lots of people get carried away in the moment of a relationship, regret it, and later want to figure out a way to slow things down a bit. The key to gracefully slowing things down is to make sure he knows that you really enjoyed your time with him and enjoyed kissing him, too. Tell him as much because this will stroke his ego a bit. If you compliment him a bit then it will blunt the impact of telling him you don't want to make out with him. Most guys take themselves pretty seriously when it comes to being physically intimate with girls (even when that's just making out) and being told to back off can be a bit of a shot through the heart, but being complimentary to them will smooth things over considerably.

After the initial disappointment or surprise wears off, this guy will eventually grow to appreciate your honesty and that honesty will do wonders for the general tenor of communication in your relationship. Communication can sometimes be tense in the initial stages of a relationship and a concerted effort by one person to take a risk and open those lines of communication can be what it takes to throw that door wide open and truly provide you with a lot more progress in a short amount of time than any other single thing you can do. So be honest, be open, fluff up his ego a bit, and you'll be more than satisfied with the eventual outcome.

Tags: ask a guy, advice, relationships, kissing, taking your time, slowing down

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So Much For Hooking Up

Here is the deal - I don't know what to think. My ex of three years and I broke up in October because he cheated and at that point did not want to work it out because he said I deserve better. When we broke up, he still lived in my place for two months. He said he wanted his space, so I gave it to him. He would come home and I would ignore him. Well, when I would ignore him he would try to get my attention. He would throw candy at me and clothes and walk in and say "what up" - things like that. When I asked him about it he had no clue what I was talking about.

We went to a party for our mutual friend and all night at the party, he kept giving me the peace sign and taking my drinks away from me. When he finally moved we had little contact. This past week, I went with him to get a phone. He offered a hug and I declined, even though I really wanted one. After that he said, "I thought you might have wanted sex." I said, "well are you offering?" Next thing you know, we had sex but he did things I loved to do during sex and would rarely do before. He was kissing me a lot and hugging me. What do you think will happen next? I have been writing him I have also tried to engage more sex, but he declines it. What do I do? Help!

littleone | age 21 | March 13, 2010

Daniel says...

This guy wanted sex from you - pure and simple. In fact, he may have just wanted sex in general. At first it probably appeared as though he wanted something more, perhaps even a relationship, but that's precisely what he wanted you to think. After not talking for so long, he probably hoped he would find you somewhat vulnerable to his advances. It is likely his increased physicality during sex (doing the things you like) was due to the fact that he probably hadn't had sex in a while, either. Rather than seeming robotic or repetitive, he was excited about sex - perhaps for the first time in quite a while. This showed itself in him being more interested and more engaged in your sexual encounter.

What will happen next? Most likely nothing. He had sex with you and either that's all he wanted or he now views it as a mistake. The two of you went quite a while without speaking and then hooked up essentially randomly after running into one another at a party. After hooking up, you suddenly showed an interest in staying in touch with him - a level of interest that he may have found surprising. His recent behavior supports this thought as he now declines chances to have sex with you and you imply that he has been generally limited his availability to you since this happened. At this point, it's best to move on and avoid falling victim to any future desires for sex that he may have. He broke up with you, so until he demonstrates a true interest in you (without simply desiring sex) there is no reason to expect that anything has changed.

Tags: ask a guy, advice, relationships, hooking up, relationships with exes

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Keep Things Casual And He’ll Sort Things Out

I dated a guy for a few months, but he was hot and cold. Sometimes he would shower me with texts and sometimes I wouldn't hear from him for days. A week and a half ago he got really intense. We spent our first night at his place. He was traveling and told me he would let me know when he got back. I went out that night with friends and saw him at the bar. I approached him and said hi and he was cold. After he left I texted him and said "ouch".

He figured out where my friends and I had gone and followed us there. We talked and had a nice night. The next day I didn't hear from him. I called him the following day and we had a good discussion. I told him he wasn't treating me well and he explained he has not gotten over his ex. He really likes me but cannot let her go. He said all this was not fair to me and that he needs some time to figure this out. I said that was fine and it was a congenial parting.

The confusing part was that as he was leaving we kissed and hugged and I said, "I guess this is goodbye." He said he didn't think so, that he liked me too much for it to be goodbye. Was he just being nice? I realize he is conflicted about these relationships but I don't know if he really means he will be back or if he was just being nice.

hoops | age 42 | March 13, 2010

Daniel says...

This guy was literally seconds away from never having to talk to you again if he didn't want to - the most awkward part of your conversation was over and all he had to do was watch you walk away. The fact that he basically kept you from walking away and put himself on the hook to maintain some level of friendship indicates that he really does want to continue your friendship. It may even mean he would be open to dating you more formally in the future. You need to consider the whole collection of this guy's actions - not just one or two incidents in isolation. His actions so far seem fairly typical of a guy in the early stages of a relationship - and his "parting words" to you indicated that they didn't really intend for them to be parting words at all.

This guy appears to have his head on pretty straight. He was able to recognize that he was still hung up on his ex and he didn't want to drag you through that trouble. This is both admirable and indicative that this guy seems to respect girls a lot. I'm not sure what to make of his "I'm traveling but I'm really at the bar" episode, but everyone should be allowed at least one mistake - no one is perfect. I'd say you should keep in touch with this guy very casually but not terribly often. If you contact him too much he may start to feel as though you are pressuring him to date you. By only occasionally staying in touch with him you make sure you stay on his mind from time to time but you do so in a very low key way.

Tags: ask a guy, advice, relationships, gauging interest, patience, hot and cold

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Why Does His Friend Matter?

I really like a guy who I recently met. I went on a date with him and it seemed so perfect. But his best friend likes me and was mad that I didn't like him as much as the guy I did go out with. The guy I went out with said he really likes me but he can't do that to his best friend so he was just going to back down. I tried to tell him not to because I like him but he insisted.

I tried to set things straight, which only made it worse. Then I waited a few hours and texted him and told him I'd really like to chill tonight and talk and he never replied. I really like him and he told me he likes me but I don't know what to do. I just want to keep dating him but I won't be "officially" back to my hometown (where I met him) until summer. What do I do?

alwaystheirbro | age 19 | March 12, 2010

Daniel says...

The first thing you need to do is calm down a little. What you're trying to do right now is essentially manipulate someone into liking you. If you're a regular reader, you probably see me giving advice about how to cultivate interest in someone and wonder what the difference is. The main difference is that in those cases, you're not manipulating someone - I'm merely giving advice to someone as to how to put their best foot (or face, as the case may be) forward. In your situation, this guy has very clearly indicated that he is concerned about his friend's reaction, values his friendship, and as a result will not do anything with you to risk that. This is really a position that neither asks nor leaves room for bargaining.

The best thing to do at this point is to back off a little and focus on being this guy's friend. That's what he needs right now. You can talk and hang out together on occasion, but don't be offended if he wants to limit things a little. It sounds like his friend might be a little jealous and it's not your place to meddle in his friendship. If I were in his place, I wouldn't be willing to coddle my friend like that, but perhaps when I was younger it would have been a different story. This is a lesson he needs to learn on his own. In the mean time, don't put all your relationship eggs in this guy's basket. If he doesn't want to date you right now, then that doesn't mean you should be waiting around for the time when he finally wakes up. Keep your options open - you never know when "the right guy" may come along.

Tags: ask a guy, advice, relationships, dating, friendships

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I’m Not Going To Cheat

I think my boyfriend, despite what he says, doesn't trust me. We've been together for five years and I've never been unfaithful to him (he cheated on me with a mutual friend for four months), but I live an hour away for college. As a result, I spend more time with my college friends, who happen to be male, than with him. It makes him insecure and we've been fighting a lot about it lately. He says he wouldn't be insecure if I called more, but he was like this before I moved away, too. He was even jealous of my best girl friend (and I am straight!). It's just much more obvious now that I'm away and can't reassure him as often.

The couple of guys I hang out with here are telling me they feel bad for "causing" problems between my boyfriend and me. One of them told me that his dad cheated on his mom and ever since then, his dad would get really hostile whenever his mom did anything because he thought she would cheat on him; so now he's afraid the same might be happening to my boyfriend and me.

I don't know what to do. I can't help that my friends are male. I don't want to have to stop seeing them just to make him comfortable, but I also don't want to do anything to make him feel that kind of hurt. I've been trying to call more often and I'm completely honest about what I'm doing when we talk, but I can tell he still feels left out.

Anonymous | age 21 | March 12, 2010

Daniel says...

Your boyfriend's actions smack of someone who simply lacks self-confidence. Often when people cheat it's either because of a feeling of entitlement (think Tiger Woods) or because of a complete lack of self-confidence. This low confidence or self-esteem results in cheating because they find someone who is willing to boost their ego. They feel a little invincible because they manage to become intimate and maintain two relationships simultaneously. Unfortunately, this high-flying feeling will result in the complete opposite feeling once the relationship is discovered. Once you found out that he cheated, your boyfriend likely became paralyzed with the fear that you would cheat on him to "get even." As unrealistic as this may be, he knows how he felt when he was with the other girl and he knows he did something wrong.

Your relationship survived your boyfriend's infidelity, so you should be fully capable of talking to one another in an upfront and honest manner. Tell him exactly what you're seeing. You can even tell him that you know he's afraid that you'll cheat to get even. After you've explained this, tell him that the thought is completely unreasonable and that you won't cheat on him. If your boyfriend doesn't trust you, then that is a very serious issue - one that can potentially jeopardize your relationship. If your boyfriend can't get over this, then you do need to consider whether this relationship is right for you. You're in college; it shouldn't be your job to coddle your boyfriend and constantly reassure him that your feelings for him haven't changed.

Tags: ask a guy, advice, relationships, cheating, getting even, self-esteem

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Mixed Messages

I have a problem with my best guy friend. And by "problem," I mean that I feel like I'm in love with him. We're both 20 years old and we go to the same university. He and I have been very good friends for about five years and about six months ago, he broke up with his girlfriend of two years. We've become even closer since then. But I don't know how he feels about me; I have asked, but he sends me the most mixed signals.

For the first few months after he broke up with his girlfriend, it was just us reconnecting and becoming close as friends again. I was in a relationship at the time, too, so it was strictly friends between us. That guy and I ended up not working out, and shortly after, when I was hanging out with my friend, we ended up making out a little...but we sort of pretended it never happened.

He's sort of obsessed with finding his true love, and he really wants to get married soon and all that. He talks to me about everything, all of his hopes and fears and dreams, but also about girls he's interested in. But then when I mention somebody that I may be interested in dating he gets upset and asks me not to talk about stuff like that because "he still sees me as more than a friend." He says he knows he talks about other girls, but he doesn't talk about them seriously, and it bugs him to hear about me with other guys.

Talk about mixed signals!

So I decided a few weeks ago that I was just done with all this, because I hate feeling like I love him but there's nothing I can do, and I just pulled the whole, "I'm so glad you're my friend. You're such a good friend" thing to hammer the point home. I even said I saw him as a brother! He told me not to say that because he knows that we're more than that. Awesome, so he just wants to keep me hanging on? All this time he's still a great friend to me, though. He's protective, caring, he bends over backwards to cheer me up when I've had a bad day, offers to run errands for me and lots of other stuff. He tells me how much he cares about me.

I just don't know what to do. Last week I was upset and just done, and he and I got in a big fight about something stupid and I deleted him from my Facebook. He messaged me the same day asking why I was throwing away our friendship and he made me feel bad for cutting off contact. Now it's exactly where it was before!

What am I supposed to do? He's still a good friend, but maybe it's just not worth it if he's going to keep playing games with my feelings. He'll talk to me about us getting married someday and having kids. He says that I'm the only person he could even imagine having a kid with. Why would he talk to me about that? What does he want from me?

quitesmashing | age 19 | March 11, 2010

Daniel says...

It sure sounds like he really wants to be with you, but it doesn't sound like either of you has really pushed the envelope. This includes you. You threatened him with ending your friendship, but it appears as though you never told him what you wanted from him. This is somewhat like storming into your parents' house, screaming at them, announcing you're so mad at them and that you're moving out and never stating what they did that made you so mad. Aside from that, you catch more flies with honey than with vinegar. Coming into a discussion with a "hellfire and damnation" attitude will set people on their heels and force them into a defensive viewpoint. By engaging in informative discussions that tell people what you're feeling and what your needs and desires are, you will be much more likely to get what you want.

The one thing that is obvious in all this is the fact that you are comfortable telling this guy just about anything. Take advantage of this! Sit down with him, tell him exactly what you're seeing and what his behavior is appearing as to you. Then tell him how this makes you feel. It's important that you start with the facts because facts are not debatable. Then tell him how you feel and what you want from him. Explain your feelings for him and your desire for a relationship with him that is more than just a friendship. Your friendship has proven to be fairly resilient, so even if the conversation goes well, I suspect that you will be able to maintain that friendship should the conversation not turn out how you would like. At the same time, you could always opt to discontinue your friendship; that is your prerogative. He does like you and is probably just unsure how to proceed. Getting your feelings out on the table may help push things along, but it doesn't appear to be likely to do any significant harm.

Tags: ask a guy, advice, relationships, gauging interest, converting a friendship, growing a relationship

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Investing My Time

I just started dating this guy about a month ago. He is all the things I have been looking for in a man. He is kind, sweet, understanding, God-fearing, motivated, and more. He calls daily and takes me out weekly, but when I asked what is possible between us, he says he thinks that everything is great that we would be compatible in certain areas but he wants to wait some time before making a decision. I can respect that, but I don't want to keep taking calls daily and spending time on the phone if he is not sure. I think I should date him and others until he decides or until I decide. I don't want to push him away, but I don't want to talk daily and act as if this is a relationship when it's not. I don't want to be confused. Should I back up or just let things flow the way they have been?

modesty1178 | age 31 | March 11, 2010

Daniel says...

Many people (and this goes for guys and girls) need some time to truly analyze a relationship and decide whether it is the best thing for them going forward. In many cases, this takes more than a month. Sometimes, things just "click" and a couple finds themselves unavoidably attracted to one another, but that is certainly not always the case. As people get older, they become less willing to take overt risks in relationships and more inclined to take things slower and let things develop naturally. When we're teenagers, we want to meet someone, flirt with them, and jump into exclusive dating at the blink of an eye. But as we get more "wise" in the ways of the world, we tend to take our time. This is exactly what this guy is doing, so I wouldn't be concerned that he is playing you.

You would be well-advised to take the same approach. Consider carefully whether this guy is right for you and let things progress naturally. You've only been dating for a month so, despite the fact that he "takes you out weekly," you have only been on four real dates. This is certainly enough to establish whether you are interested in this guy, but it's understandable that he is unable to know yet whether he wants to date you exclusively. Try asking him on a date or two. Don't overdo it, though, because you don't want him to feel suffocated. Two dates per week should be about the maximum at this point, but by the time you've been dating for four months, you shouldn't be afraid to be seeing one another three or four times per week - even if it's just to say hi or grab a cup of coffee. Eventually, a conversation about your future should just happen. But if it hasn't after three or four months, then you may need to get a conversation going.

Tags: ask a guy, advice, relationships, dating, gauging interest, getting to know your significant other

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